CN110312718B - Heterocyclene derivatives as pest control agents - Google Patents

Heterocyclene derivatives as pest control agents Download PDF

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CN110312718B
CN110312718B CN201880012984.1A CN201880012984A CN110312718B CN 110312718 B CN110312718 B CN 110312718B CN 201880012984 A CN201880012984 A CN 201880012984A CN 110312718 B CN110312718 B CN 110312718B
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cycloalkyl
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CN110312718A (en
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D·维尔基
D·哈格
L·霍夫梅斯特
N·考施-布希斯
M·莫斯林
M·维洛特
R·菲舍尔
K·伊尔格
U·戈杰恩斯
A·特伯格
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Bayer CropScience AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Abstract

The invention relates to novel compounds of formula (I), wherein X, R 1 、R 2 、R 3 And n have the meanings indicated in the description, to their use as acaricides and/or insecticides for controlling animal pests, and to processes and intermediate products for preparing them.

Description

Heterocyclene derivatives as pest control agents
The present invention relates to heterocyclic derivatives of the formula (I), to their use as acaricides and/or insecticides for controlling animal pests, in particular arthropods and especially insects and arachnids, and to processes and intermediates for preparing them.
Heterocyclic derivatives having insecticidal properties have been described in the following documents: for example WO 2010/125985, WO 2012/074135, WO 2012/086848, WO 2013/018928, WO 2013/180193, WO 2013/191113, WO 2014/142292, WO 2014/148451, WO 2015/000715, WO 2016/124563, WO 2016/124557557, WO 2015/121136, WO 2015/133603, WO 2015/198859, WO 2015/002211, WO 2015/071180, WO 2015/091945, WO 2016/005263, WO 2016/039441, WO 2015/198817, WO 2016/041819, WO 2016/039441, WO 2015/039441 WO 2016/039444, WO 2016/026848, WO 2016/023954, WO 2016/020286, WO 2016/046071, WO 2016/058928, WO 2016/059145, WO 2016/071214, WO 2016/091731, WO 2016/096584, WO 2016/107742, WO 2016/107831, WO 2016/113155, WO 2016/116338, WO 2016/121997, WO 2016/125621, WO 2016/125622, WO 2016/129684, WO 2016/142326, WO 2016/142327, WO 2016/169882, and WO 2016/169886.
Modern crop protection compositions have to meet a number of requirements, for example requirements relating to degree, persistence and their spectrum of action and possible use. The problems of toxicity, retention of beneficial species and pollinators, environmental characteristics, application rates, binding to other active compounds or formulation auxiliaries play a role, as do the problems of complexity involved in the synthesis of the active ingredients, and resistance may also occur, to mention only a few parameters. For all these reasons, the search for new crop protection compositions cannot be regarded as complete and there is a continuing need for new compounds having improved properties compared with the known compounds, at least in individual respects.
It is an object of the present invention to provide compounds which in various aspects broaden the spectrum of pesticides and/or improve their activity.
Novel heterocyclic derivatives have now been found which have advantages over the known compounds, examples of which include better biological or environmental properties, more extensive application methods, better insecticidal or acaricidal action and good compatibility with crop plants. The heterocyclic derivatives may be used in combination with other compositions to improve efficacy, particularly against difficult to control insects.
The subject of the invention is therefore novel compounds of the formula (I)
Figure GDA0003969167050000021
Wherein (configuration 1-1)
R 1 Is (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Cyanoalkyl, (C) 1 -C 6 ) Hydroxyalkyl, (C) 1 -C 6 ) Alkoxy radical- (C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl, (C) 2 -C 6 ) Haloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkynyl or (C) 3 -C 8 ) A cycloalkyl group, which is a cyclic alkyl group,
R 2 is hydrogen, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Cyanoalkyl, (C) 1 -C 6 ) Hydroxyalkyl group, (C) 1 -C 6 ) Alkoxy radical- (C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl, (C) 2 -C 6 ) Alkenyloxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Haloalkenyloxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 2 -C 6 ) Cyanoalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Alkynyloxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Haloalkynyloxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Halogenated alkynyl, (C) 2 -C 6 ) Cyanoalkynyl group, (C) 3 -C 8 ) Cycloalkyl group, (C) 3 -C 8 ) Cycloalkyl- (C) 3 -C 8 ) Cycloalkyl group, (C) 1 -C 6 ) Alkyl radical- (C) 3 -C 8 ) Cycloalkyl, halo (C) 3 -C 8 ) Cycloalkyl, cyano (C) 3 -C 8 ) Cycloalkyl group, (C) 1 -C 6 ) Alkylthio- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkylthio- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylsulfinyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkylsulfinyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylsulfonyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkylsulfonyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylcarbonyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Halogenoalkylcarbonyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxycarbonyl- (C) 1 -C 6 ) Alkyl or (C) 1 -C 6 ) Halogenoalkoxycarbonyl- (C) 1 -C 6 ) An alkyl group, a carboxyl group,
R 3 is hydrogen, halogen, cyano, nitro, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Alkylthio group, (C) 1 -C 6 ) Haloalkylthio, (C) 1 -C 6 ) Alkylsulfinyl (C) 1 -C 6 ) Haloalkylsulfinyl, (C) 1 -C 6 ) Alkylsulfonyl group, (C) 1 -C 6 ) Haloalkylsulfonyl, SCN, (C) 1 -C 6 ) Alkylcarbonyl, (C) 1 -C 6 ) Haloalkyl carbonyl, (C) 1 -C 6 ) Alkoxycarbonyl, (C) 1 -C 6 ) Halogenated alkoxycarbonyl, aminocarbonyl, (C) 1 -C 6 ) Alkylaminocarbonyl, di (C) 1 -C 6 ) Alkylaminocarbonyl, (C) 1 -C 6 ) Haloalkylaminocarbonyl group, (C) 3 -C 8 ) Cycloalkylaminocarbonyl, aminothiocarbonyl, (C) 1 -C 6 ) Alkylamino thiocarbonyl, di (C) 1 -C 6 ) Alkylaminothiocarbonyl (C) 1 -C 6 ) Haloalkylaminothiocarbonyl, (C) 3 -C 8 ) Cycloalkylaminothiocarbonyl, amino, (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Haloalkylamino, di (C) 1 -C 6 ) Alkylamino radical, (C) 3 -C 8 ) Cycloalkylamino, (C) 1 -C 6 ) Alkylsulfonylamino group, (C) 1 -C 6 ) Alkylcarbonylamino, (C) 1 -C 6 ) Haloalkylcarbonylamino, (C) 1 -C 6 ) Alkylcarbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Haloalkyl carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 3 -C 8 ) Cycloalkylcarbonylamino group, (C) 3 -C 8 ) Cycloalkyl carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Alkylthio carbonylamino ((C) 1 -C 6 )alkylthiocarbonylamino)、(C 1 -C 6 ) Haloalkylthiocarbonylamino group, (C) 1 -C 6 ) Cyclothiocarbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Halogenoalkylthio carbonyl- (C) 1 -C 6 ) Alkylamino ((C) 1 -C 6 )haloalkylthiocarbonyl-(C 1 -C 6 )alkylamino)、(C 3 -C 8 ) Cycloalkylthio (cycloalkylthio) carbonylamino group, (C) 3 -C 8 ) Cycloalkanethiocarbonyl- (C) 1 -C 6 ) Alkyl radicalAlkylamino radical, (C) 2 -C 6 ) Alkenyl, (C) 2 -C 6 ) Haloalkenyl, (C) 2 -C 6 ) Cyanoalkenyl, (C) 3 -C 8 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 2 -C 6 ) Alkynyl or (C) 2 -C 6 ) Haloalkynyl, or aryl or heteroaryl, each of which is optionally mono-or polysubstituted by identical or different substituents, wherein (in the case of heteroaryl) at least one carbonyl group may optionally be present, and the possible substituents in each case are as follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN, SF 5 III (C) 1 -C 6 ) Alkylsilyl group, (C) 3 -C 8 ) Cycloalkyl group, (C) 3 -C 8 ) Cycloalkyl- (C) 3 -C 8 ) Cycloalkyl group, (C) 1 -C 6 ) Alkyl- (C) 3 -C 8 ) Cycloalkyl, (C) 1 -C 6 ) Haloalkyl- (C) 3 -C 8 ) Cycloalkyl, halo (C) 3 -C 8 ) Cycloalkyl, cyano (C) 3 -C 8 ) Cycloalkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Cyanoalkyl, (C) 1 -C 6 ) Hydroxyalkyl, hydroxycarbonyl- (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Alkoxycarbonyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl, (C) 2 -C 6 ) Haloalkenyl, (C) 2 -C 6 ) Cyanoalkenyl, (C) 3 -C 8 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Halogenated alkynyl, (C) 2 -C 6 ) Cyanoalkynyl group, (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Cyanoalkoxy group, (C) 1 -C 6 ) Alkoxycarbonyl- (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Alkoxy radical- (C 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Alkoxy radicalImino group, (C) 1 -C 6 ) Haloalkoxyimino group, (C) 1 -C 6 ) Alkylthio, (C) 1 -C 6 ) Haloalkylthio, (C) 1 -C 6 ) Alkoxy radical- (C 1 -C 6 ) Alkylthio group, (C) 1 -C 6 ) Alkylthio- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylsulfinyl (C) 1 -C 6 ) Haloalkylsulfinyl, (C) 1 -C 6 ) Alkoxy radical- (C 1 -C 6 ) Alkylsulfinyl (C) 1 -C 6 ) Alkylsulfinyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylsulfonyl group, (C) 1 -C 6 ) Haloalkylsulfonyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkylsulfonyl, (C) 1 -C 6 ) Alkylsulfonyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylsulfonyloxy, (C) 1 -C 6 ) Haloalkylsulfonyloxy, (C) 1 -C 6 ) Alkylcarbonyl group, (C) 1 -C 6 ) Haloalkyl carbonyl, (C) 1 -C 6 ) Alkylcarbonyloxy, (C) 1 -C 6 ) Alkoxycarbonyl, (C) 1 -C 6 ) Halogenated alkoxycarbonyl, aminocarbonyl, (C) 1 -C 6 ) Alkylaminocarbonyl, di (C) 1 -C 6 ) Alkylaminocarbonyl, (C) 1 -C 6 ) Haloalkylaminocarbonyl group, (C) 2 -C 6 ) Alkenylaminocarbonyl, di (C) 2 -C 6 ) Alkenylaminocarbonyl group, (C) 3 -C 8 ) Cycloalkylaminocarbonyl group, (C) 1 -C 6 ) Alkylsulfonylamino group, (C) 1 -C 6 ) Alkylamino radical, di (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Haloalkylamino, (C) 3 -C 8 ) Cycloalkylamino, aminosulfonyl, (C) 1 -C 6 ) Alkylaminosulfonyl, di (C) 1 -C 6 ) Alkylaminosulfonyl, (C) 1 -C 6 ) Alkylsulfoxide imino (alkylsulfoxide), aminothiocarbonyl, (C) 1 -C 6 ) Alkyl amino sulfurSubstituted carbonyl, di (C) 1 -C 6 ) Alkylaminothiocarbonyl group, (C) 1 -C 6 ) Haloalkylaminothiocarbonyl, (C) 3 -C 8 ) Cycloalkylaminothiocarbonyl, (C) 1 -C 6 ) Alkylcarbonylamino group, (C) 1 -C 6 ) Haloalkylcarbonylamino, (C) 1 -C 6 ) Alkylcarbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Halogenoalkylcarbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 3 -C 8 ) Cycloalkylcarbonylamino group, (C) 3 -C 8 ) Cycloalkyl carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Alkylthio carbonylamino group, (C) 1 -C 6 ) Haloalkylthiocarbonylamino group, (C) 1 -C 6 ) Alkylthio carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Halogenoalkylthio carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 3 -C 8 ) Cycloalkylthio carbonylamino group, (C) 3 -C 8 ) Cycloalkanethiocarbonyl- (C) 1 -C 6 ) Alkylamino, heteroaryl, oxoheteroaryl, haloheteroaryl, halooxoheteroaryl, cyanoheteroaryl, cyanooxoheteroaryl, (C) 1 -C 6 ) Haloalkyl heteroaryl or (C) 1 -C 6 ) A haloalkyl-oxo-heteroaryl group, a pharmaceutically acceptable salt thereof,
x is a heteroaromatic 9-or 12-membered fused bicyclic or tricyclic ring system selected from Q1 to Q12
Figure GDA0003969167050000051
R 4 Is hydrogen, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Cyanoalkyl, (C) 1 -C 6 ) Hydroxyalkyl, (C) 1 -C 6 ) Alkoxy radical- (C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl, (C) 2 -C 6 ) Alkenyloxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Haloalkenyloxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 2 -C 6 ) Cyanoalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkynyl or (C) 3 -C 8 ) A cycloalkyl group,
R 5 、R 6 independently hydrogen, cyano, halogen, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl, (C) 2 -C 6 ) Haloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkynyl group, (C) 3 -C 8 ) Cycloalkyl group, (C) 3 -C 8 ) Cycloalkyl- (C) 3 -C 8 ) Cycloalkyl, (C) 1 -C 6 ) Alkyl radical- (C) 3 -C 8 ) Cycloalkyl group, (C) 1 -C 6 ) Haloalkyl- (C) 3 -C 8 ) Cycloalkyl, cyano- (C) 3 -C 8 ) Cycloalkyl, halo (C) 3 -C 8 ) Cycloalkyl group, (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Alkoxyimino group, (C) 1 -C 6 ) Haloalkoxyimino group, (C) 1 -C 6 ) Alkylthio group, (C) 1 -C 6 ) Haloalkylthio, (C) 1 -C 6 ) Alkylsulfinyl (C) 1 -C 6 ) Haloalkylsulfinyl, (C) 1 -C 6 ) Alkylsulfonyl, (C) 1 -C 6 ) Haloalkylsulfonyl, (C) 1 -C 6 ) Alkylsulfonyloxy, (C) 1 -C 6 ) Haloalkylsulfonyloxy, (C) 1 -C 6 ) Alkylcarbonyl, (C) 1 -C 6 ) Haloalkyl carbonyl, aminocarbonyl, (C) 1 -C 6 ) Alkylaminocarbonyl, di (C) 1 -C 6 ) Alkylaminocarbonyl, (C) 1 -C 6 ) Alkylsulfonylamino group, (C) 1 -C 6 ) Alkylamino radical, di (C) 1 -C 6 ) Alkylamino, aminosulfonyl, (C) 1 -C 6 ) Alkylaminosulfonyl or di (C) 1 -C 6 ) An alkylaminosulfonyl group, an alkyl amino group,
n is 0, 1 or 2.
In another embodiment, the invention relates to compounds of formula (I) wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 1-1, wherein R is R if X is Q7 3 Not being hydrogen, halogen, cyano, nitro, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Alkylthio group, (C) 1 -C 6 ) Haloalkylthio, (C) 1 -C 6 ) Alkylsulfinyl (C) 1 -C 6 ) Haloalkylsulfinyl, (C) 1 -C 6 ) Alkylsulfonyl or (C) 1 -C 6 ) A haloalkylsulfonyl group.
Configuration 1-2
R 1 Is (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Cyanoalkyl, (C) 1 -C 6 ) Hydroxyalkyl group, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl, (C) 2 -C 6 ) Haloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkynyl or (C) 3 -C 8 ) A cycloalkyl group, which is a cyclic alkyl group,
R 2 is hydrogen, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Cyanoalkyl, (C) 1 -C 6 ) Hydroxyalkyl group, (C) 1 -C 6 ) Alkoxy radical- (C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl, (C) 2 -C 6 ) Alkenyloxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Halogenoalkenyloxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 2 -C 6 ) Cyanoalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Alkynyloxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Haloalkynyloxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Haloalkynyl group, (C) 2 -C 6 ) Cyanoalkynyl, (C) 3 -C 8 ) Cycloalkyl group, (C) 3 -C 8 ) Cycloalkyl- (C) 3 -C 8 ) Cycloalkyl group, (C) 1 -C 6 ) Alkyl radical- (C) 3 -C 8 ) Cycloalkyl, halo (C) 3 -C 8 ) Cycloalkyl, cyano (C) 3 -C 8 ) Cycloalkyl, (C) 1 -C 6 ) Alkylthio- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkylthio- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylsulfinyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkylsulfinyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylsulfonyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkylsulfonyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylcarbonyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl carbonyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxycarbonyl- (C) 1 -C 6 ) Alkyl or (C) 1 -C 6 ) Halogenoalkoxycarbonyl- (C) 1 -C 6 ) An alkyl group, which is a radical of an alkyl group,
R 3 is hydrogen, halogen, cyano, nitro, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Alkylthio group, (C) 1 -C 6 ) Haloalkylthio, (C) 1 -C 6 ) Alkylsulfinyl (C) 1 -C 6 ) Haloalkylsulfinyl, (C) 1 -C 6 ) Alkylsulfonyl group, (C) 1 -C 6 ) Haloalkylsulfonyl, SCN, (C) 1 -C 6 ) Alkylcarbonyl group, (C) 1 -C 6 ) Haloalkylcarbonyl group, (C) 1 -C 6 ) Alkoxycarbonyl, (C) 1 -C 6 ) Halogenated alkoxycarbonyl, aminocarbonyl, (C) 1 -C 6 ) Alkylaminocarbonyl, di (C) 1 -C 6 ) Alkylaminocarbonyl, (C) 1 -C 6 ) Haloalkylaminocarbonyl group, (C) 3 -C 8 ) Cycloalkylaminocarbonyl, aminothiocarbonyl, (C) 1 -C 6 ) Alkylamino thiocarbonyl, di (C) 1 -C 6 ) Alkylaminothiocarbonyl group, (C) 1 -C 6 ) Haloalkylaminothiocarbonyl, (C) 3 -C 8 ) Cycloalkylaminothiocarbonyl, amino, (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Haloalkylamino, di (C) 1 -C 6 ) Alkylamino radical, (C) 3 -C 8 ) Cycloalkylamino group, (C) 1 -C 6 ) Alkylsulfonylamino group, (C) 1 -C 6 ) Alkylcarbonylamino, (C) 1 -C 6 ) Haloalkylcarbonylamino, (C) 1 -C 6 ) Alkylcarbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Haloalkyl carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 3 -C 8 ) Cycloalkylcarbonylamino group, (C) 3 -C 8 ) Cycloalkyl carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Alkylthio carbonyl amino, (C) 1 -C 6 ) Halogenoalkylthio carbonylamino, (C) 1 -C 6 ) Alkylthio carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Halogenoalkylthio carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 3 -C 8 ) Cycloalkylthiocarbonylamino group, (C) 3 -C 8 ) Cycloalkanethiocarbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 2 -C 6 ) Alkenyl, (C) 2 -C 6 ) Haloalkenyl, (C) 2 -C 6 ) Cyanoalkenyl, (C) 3 -C 8 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Halogenated alkynyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkynyl, (C) 3 -C 6 ) Cycloalkyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylamino carbonylamino, di (C) 1 -C 6 ) Alkylamino carbonylamino group, (C) 3 -C 6 ) Cycloalkylaminocarbonylamino, (C) 1 -C 6 ) Haloalkylaminocarbonylamino, (C) 1 -C 6 ) Alkylamino carbonyl- (C) 1 -C 6 ) Alkylamino radical, di (C) 1 -C 6 ) Alkylamino carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylaminocarbonyl- (C) 1 -C 6 ) Alkylamino or (C) 1 -C 6 ) Halogenoalkylaminocarbonyl- (C) 1 -C 6 ) An alkylamino group,
or is aryl, heteroaryl, cyclopentenyl or cyclohexenyl, each of which is optionally mono-or polysubstituted by identical or different substituents, wherein (in the case of heteroaryl) at least one carbonyl group may optionally be present, and the possible substituents in each case are the following: cyano, carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN, SF 5 III (C) 1 -C 6 ) Alkylsilyl group, (C) 3 -C 8 ) Cycloalkyl group, (C) 3 -C 8 ) Cycloalkyl- (C) 3 -C 8 ) Cycloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 8 ) Cycloalkyl, (C) 1 -C 6 ) Haloalkyl- (C) 3 -C 8 ) Cycloalkyl, halo (C) 3 -C 8 ) Cycloalkyl, cyano (C) 3 -C 8 ) Cycloalkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Cyanoalkyl, (C) 1 -C 6 ) Hydroxyalkyl, hydroxycarbonyl- (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Alkoxycarbonyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy radical- (C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl, (C) 2 -C 6 ) Haloalkenyl, (C) 2 -C 6 ) Cyanoalkenyl, (C) 3 -C 8 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkynyl group, (C) 2 -C 6 ) Cyanoalkynyl group, (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Cyanoalkoxy group, (C) 1 -C 6 ) Alkoxycarbonyl- (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Alkoxyimino group, (C) 1 -C 6 ) Haloalkoxyimino group, (C) 1 -C 6 ) Alkylthio, (C) 1 -C 6 ) Haloalkylthio, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkylthio group, (C) 1 -C 6 ) Alkylthio- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylsulfinyl (C) 1 -C 6 ) Haloalkylsulfinyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkylsulfinyl (C) 1 -C 6 ) Alkylsulfinyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylsulfonyl, (C) 1 -C 6 ) Haloalkylsulfonyl, (C) 1 -C 6 ) Alkoxy radical- (C 1 -C 6 ) Alkylsulfonyl group, (C) 1 -C 6 ) Alkylsulfonyl- (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylsulfonyloxy, (C) 1 -C 6 ) Haloalkylsulfonyloxy, (C) 1 -C 6 ) Alkylcarbonyl, (C) 1 -C 6 ) Haloalkylcarbonyl group, (C) 1 -C 6 ) Alkylcarbonyloxy, (C) 1 -C 6 ) Alkoxycarbonyl, (C) 1 -C 6 ) Halogenated alkoxycarbonyl, aminocarbonyl, (C) 1 -C 6 ) Alkylaminocarbonyl, di (C) 1 -C 6 ) Alkylaminocarbonyl, (C) 1 -C 6 ) Haloalkylaminocarbonyl, (C) 2 -C 6 ) Alkenylaminocarbonyl, bis(C 2 -C 6 ) Alkenylaminocarbonyl group, (C) 3 -C 8 ) Cycloalkylaminocarbonyl group, (C) 1 -C 6 ) Alkylsulfonylamino group, (C) 1 -C 6 ) Alkylamino radical, di (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Haloalkylamino, (C) 3 -C 8 ) Cycloalkylamino, aminosulfonyl, (C) 1 -C 6 ) Alkylaminosulfonyl, di (C) 1 -C 6 ) Alkylaminosulfonyl, (C) 1 -C 6 ) Alkyl sulfoxide imino, aminothiocarbonyl, (C) 1 -C 6 ) Alkylamino thiocarbonyl, di (C) 1 -C 6 ) Alkylaminothiocarbonyl (C) 1 -C 6 ) Haloalkylaminothiocarbonyl, (C) 3 -C 8 ) Cycloalkylaminothiocarbonyl, (C) 1 -C 6 ) Alkylcarbonylamino group, (C) 1 -C 6 ) Haloalkylcarbonylamino, (C) 1 -C 6 ) Alkylcarbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Halogenoalkylcarbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 3 -C 8 ) Cycloalkylcarbonylamino group, (C) 3 -C 8 ) Cycloalkyl carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Alkylthio carbonylamino group, (C) 1 -C 6 ) Haloalkylthiocarbonylamino group, (C) 1 -C 6 ) Alkylthio carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 1 -C 6 ) Halogenoalkylthio carbonyl- (C) 1 -C 6 ) Alkylamino radical, (C) 3 -C 8 ) Cycloalkylthiocarbonylamino group, (C) 3 -C 8 ) Cycloalkylthiocarbonyl- (C) 1 -C 6 ) Alkylamino, heteroaryl, oxoheteroaryl, haloheteroaryl, halooxoheteroaryl, cyanoheteroaryl, cyanooxoheteroaryl, (C) 1 -C 6 ) Haloalkyl heteroaryl or (C) 1 -C 6 ) A haloalkyl-oxo-heteroaryl group, a pharmaceutically acceptable salt thereof,
x is a heteroaromatic 9-or 12-membered fused bicyclic or tricyclic ring system selected from Q1 to Q12
Figure GDA0003969167050000091
R 4 Is hydrogen, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Cyanoalkyl, (C) 1 -C 6 ) Hydroxyalkyl, (C) 1 -C 6 ) Alkoxy radical- (C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl, (C) 2 -C 6 ) Alkenyloxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Haloalkenyloxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 2 -C 6 ) Cyanoalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkynyl or (C) 3 -C 8 ) A cycloalkyl group,
R 5 、R 6 independently hydrogen, cyano, halogen, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl, (C) 2 -C 6 ) Haloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkynyl group, (C) 3 -C 8 ) Cycloalkyl group, (C) 3 -C 8 ) Cycloalkyl- (C) 3 -C 8 ) Cycloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 8 ) Cycloalkyl group, (C) 1 -C 6 ) Haloalkyl- (C) 3 -C 8 ) Cycloalkyl, cyano- (C) 3 -C 8 ) Cycloalkyl, halo (C) 3 -C 8 ) Cycloalkyl group, (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Alkoxyimino group, (C) 1 -C 6 ) Haloalkoxyimino group, (C) 1 -C 6 ) Alkylthio group, (C) 1 -C 6 ) Haloalkylthio, (C) 1 -C 6 ) Alkylsulfinyl (C) 1 -C 6 ) Haloalkylsulfinyl, (C) 1 -C 6 ) Alkylsulfonyl, (C) 1 -C 6 ) Haloalkylsulfonyl, (C) 1 -C 6 ) Alkylsulfonyloxy group, (C) 1 -C 6 ) Haloalkylsulfonyloxy, (C) 1 -C 6 ) Alkylcarbonyl group, (C) 1 -C 6 ) Haloalkylcarbonyl, aminocarbonyl, (C) 1 -C 6 ) Alkylaminocarbonyl, di (C) 1 -C 6 ) Alkylaminocarbonyl, (C) 1 -C 6 ) Alkylsulfonylamino group, (C) 1 -C 6 ) Alkylamino radical, di (C) 1 -C 6 ) Alkylamino, aminosulfonyl, (C) 1 -C 6 ) Alkylaminosulfonyl or di (C) 1 -C 6 ) An alkylamino sulfonyl group, which is a substituent of a heterocyclic ring,
n is 0, 1 or 2.
In another embodiment, the invention relates to compounds of formula (I), wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 1-2, wherein if X is Q7, then R is 3 Not being hydrogen, halogen, cyano, nitro, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy group, (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Alkylthio group, (C) 1 -C 6 ) Haloalkylthio, (C) 1 -C 6 ) Alkylsulfinyl (C) 1 -C 6 ) Haloalkylsulfinyl, (C) 1 -C 6 ) Alkylsulfonyl or (C) 1 -C 6 ) A haloalkylsulfonyl group.
It has furthermore been found that the compounds of the formula (I) have very good efficacy as pesticides, preferably as insecticides and/or acaricides; and also generally have very good plant compatibility, especially for crop plants.
The compounds of the invention are defined in general terms by the formula (I). Preferred substituents or ranges for the groups given in the formulae mentioned hereinbefore are indicated below:
Configuration 2-1
R 1 Preferably (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Cyanoalkyl, (C) 1 -C 4 ) Alkoxy- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Haloalkynyl or (C) 3 -C 6 ) A cycloalkyl group, which is a cyclic alkyl group,
R 2 preferably hydrogen, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Cyanoalkyl, (C) 1 -C 4 ) Hydroxyalkyl group, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkoxy- (C) 1 -C 4 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Cycloalkyl- (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkyl radical- (C) 3 -C 6 ) Cycloalkyl, halo (C) 3 -C 6 ) Cycloalkyl, cyano (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkylthio- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkylthio- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkylsulfinyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Halogenoalkylsulfinyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkylsulfonyl- (C) 1 -C 4 ) Alkyl or (C) 1 -C 4 ) Haloalkylsulfonyl- (C) 1 -C 4 ) An alkyl group, a carboxyl group,
R 3 preferably hydrogen, halogen, cyano, nitro, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Alkylthio, (C) 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) A halogenated alkylsulfinyl group,(C 1 -C 4 ) Alkylsulfonyl, (C) 1 -C 4 ) Haloalkylsulfonyl, SCN, (C) 1 -C 4 ) Alkylcarbonyl group, (C) 1 -C 4 ) Haloalkylcarbonyl group, (C) 1 -C 4 ) Alkoxycarbonyl group, (C) 1 -C 4 ) Halogenated alkoxycarbonyl, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Haloalkylaminocarbonyl group, (C) 3 -C 6 ) Cycloalkylaminocarbonyl, aminothiocarbonyl, (C) 1 -C 4 ) Alkylamino thiocarbonyl, di (C) 1 -C 4 ) Alkylaminothiocarbonyl (C) 1 -C 4 ) Haloalkylaminothiocarbonyl, (C) 3 -C 6 ) Cycloalkylaminothiocarbonyl, amino, (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkyl amino, di (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylamino, (C) 1 -C 4 ) Alkylsulfonylamino group, (C) 1 -C 4 ) Alkylcarbonylamino group, (C) 1 -C 4 ) Haloalkylcarbonylamino, (C) 1 -C 4 ) Alkylcarbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkyl carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylcarbonylamino group, (C) 3 -C 6 ) Cycloalkyl carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Alkylthio carbonylamino group, (C) 1 -C 4 ) Haloalkylthiocarbonylamino group, (C) 1 -C 4 ) Alkylthio carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Halogenoalkylthio carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylthiocarbonylamino group, (C) 3 -C 6 ) Cycloalkanethiocarbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Cyanoalkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 2 -C 4 ) Alkynyl or (C) 2 -C 4 ) A halogenated alkynyl group,
or preferably aryl or heteroaryl, each of which is optionally mono-or polysubstituted by identical or different substituents, where (in the case of heteroaryl) at least one carbonyl group may optionally be present, and the substituents which are possible in each case are the following: cyano, carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN, SF 5 Three (C) 1 -C 4 ) Alkylsilyl group, (C) 3 -C 6 ) Cycloalkyl group, (C) 3 -C 6 ) Cycloalkyl- (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Haloalkyl- (C) 3 -C 6 ) Cycloalkyl, halo (C) 3 -C 6 ) Cycloalkyl, cyano (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Cyanoalkyl, (C) 1 -C 4 ) Hydroxyalkyl, hydroxycarbonyl- (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Alkoxycarbonyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 4 ) Alkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Cyanoalkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Haloalkynyl group, (C) 2 -C 4 ) Cyanoalkynyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Cyanoalkoxy group, (C) 1 -C 4 ) Alkoxycarbonyl- (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Alkoxy- (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Alkoxyimino group, (C) 1 -C 4 ) Haloalkoxyimino group, (C) 1 -C 4 ) Alkylthio, alkylthio,(C 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 4 ) Alkylthio group, (C) 1 -C 4 ) Alkylthio- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Alkylsulfinyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkylsulfonyl, (C) 1 -C 4 ) Haloalkylsulfonyl, (C) 1 -C 4 ) Alkoxy- (C) 1 -C 4 ) Alkylsulfonyl, (C) 1 -C 4 ) Alkylsulfonyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkylsulfonyloxy group, (C) 1 -C 4 ) Haloalkylsulfonyloxy, (C) 1 -C 4 ) Alkylcarbonyl group, (C) 1 -C 4 ) Haloalkylcarbonyl group, (C) 1 -C 4 ) Alkylcarbonyloxy, (C) 1 -C 4 ) Alkoxycarbonyl group, (C) 1 -C 4 ) Halogenated alkoxycarbonyl, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Halogenated alkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 2 -C 4 ) Alkenylaminocarbonyl, di (C) 2 -C 4 ) Alkenylaminocarbonyl group, (C) 3 -C 6 ) Cycloalkylaminocarbonyl group, (C) 1 -C 4 ) Alkylsulfonylamino group, (C) 1 -C 4 ) Alkylamino radical, di (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkylamino, (C) 3 -C 6 ) Cycloalkylamino, aminosulfonyl, (C) 1 -C 4 ) Alkylaminosulfonyl, di (C) 1 -C 4 ) Alkylaminosulfonyl, (C) 1 -C 4 ) Alkyl sulfoxide imino, aminothiocarbonyl, (C) 1 -C 4 ) Alkylamino thiocarbonyl, di (C) 1 -C 4 ) Alkylaminothiocarbonyl (C) 1 -C 4 ) Haloalkylaminothiocarbonyl、(C 3 -C 6 ) Cycloalkylaminothiocarbonyl, (C) 1 -C 4 ) Alkylcarbonylamino group, (C) 1 -C 4 ) Haloalkylcarbonylamino, (C) 1 -C 4 ) Alkylcarbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkyl carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylcarbonylamino group, (C) 3 -C 6 ) Cycloalkyl carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Alkylthio carbonylamino group, (C) 1 -C 4 ) Haloalkylthiocarbonylamino group, (C) 1 -C 4 ) Alkylthio carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Halogenoalkylthio carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylthiocarbonylamino group, (C) 3 -C 6 ) Cycloalkanethiocarbonyl- (C) 1 -C 4 ) Alkylamino, heteroaryl, oxoheteroaryl, haloheteroaryl, halooxoheteroaryl, cyanoheteroaryl, cyanooxoheteroaryl, (C) 1 -C 4 ) Haloalkyl heteroaryl or (C) 1 -C 4 ) A haloalkyl oxoheteroaryl group,
X is preferably a heteroaromatic 9-or 12-membered fused bicyclic or tricyclic ring system selected from Q1 to Q12,
R 4 preferably hydrogen, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Cyanoalkyl, (C) 1 -C 4 ) Alkoxy- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkoxy- (C) 1 -C 4 ) Alkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Haloalkynyl or (C) 3 -C 6 ) A cycloalkyl group, which is a cyclic alkyl group,
R 5 、R 6 each independently of the others is preferably hydrogen, cyano, halogen, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Halogenated alkynyl, (C) 3 -C 6 ) Cycloalkyl group, (C) 3 -C 6 ) Cycloalkyl- (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkyl radical- (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Haloalkyl- (C) 3 -C 6 ) Cycloalkyl, cyano (C) 3 -C 6 ) Cycloalkyl, halo (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Alkoxyimino group, (C) 1 -C 4 ) Haloalkoxyimino group, (C) 1 -C 4 ) Alkylthio group, (C) 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkylsulfonyl group, (C) 1 -C 4 ) Haloalkylsulfonyl, (C) 1 -C 4 ) Alkylsulfonyloxy group, (C) 1 -C 4 ) Haloalkylsulfonyloxy, (C) 1 -C 4 ) Alkylcarbonyl or (C) 1 -C 4 ) A halogenated alkyl carbonyl group,
n is preferably 0, 1 or 2.
In another embodiment, the invention relates to compounds of formula (I) wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 2-1, wherein R is R if X is preferably Q7 3 Not being hydrogen, halogen, cyano, nitro, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Alkylthio, (C) 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkylsulfonyl or (C) 1 -C 4 ) A haloalkylsulfonyl group.
Configuration 2-2
R 1 Preferably (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Cyanoalkyl, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Haloalkynyl or (C) 3 -C 6 ) A cycloalkyl group, a,
R 2 Preferably hydrogen, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Cyanoalkyl, (C) 1 -C 4 ) Hydroxyalkyl, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkoxy- (C) 1 -C 4 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl group, (C) 3 -C 6 ) Cycloalkyl- (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, halo (C) 3 -C 6 ) Cycloalkyl, cyano (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Alkylthio- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkylthio- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkylsulfinyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Halogenoalkylsulfinyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkylsulfonyl- (C) 1 -C 4 ) Alkyl or (C) 1 -C 4 ) Haloalkylsulfonyl- (C) 1 -C 4 ) An alkyl group, a carboxyl group,
R 3 preferably hydrogen, halogen, cyano, nitro, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Alkylthio group, (C) 1 -C 4 ) Halogenated alkyl sulfideBase, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkylsulfonyl group, (C) 1 -C 4 ) Haloalkylsulfonyl, SCN, (C) 1 -C 4 ) Alkylcarbonyl group, (C) 1 -C 4 ) Haloalkylcarbonyl group, (C) 1 -C 4 ) Alkoxycarbonyl, (C) 1 -C 4 ) Halogenated alkoxycarbonyl, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Haloalkylaminocarbonyl, (C) 3 -C 6 ) Cycloalkylaminocarbonyl, aminothiocarbonyl, (C) 1 -C 4 ) Alkylamino thiocarbonyl, di (C) 1 -C 4 ) Alkylaminothiocarbonyl group, (C) 1 -C 4 ) Haloalkylaminothiocarbonyl, (C) 3 -C 6 ) Cycloalkylaminothiocarbonyl, amino, (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkyl amino, di (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylamino, (C) 1 -C 4 ) Alkylsulfonylamino group, (C) 1 -C 4 ) Alkylcarbonylamino group, (C) 1 -C 4 ) Haloalkylcarbonylamino, (C) 1 -C 4 ) Alkylcarbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkyl carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylcarbonylamino group, (C) 3 -C 6 ) Cycloalkyl carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Alkylthio carbonyl amino, (C) 1 -C 4 ) Halogenoalkylthio carbonylamino, (C) 1 -C 4 ) Alkylthio carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Halogenoalkylthio carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylthiocarbonylamino group, (C) 3 -C 6 ) Cycloalkanethiocarbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 2 -C 4 ) AlkeneBase, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Cyanoalkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Haloalkynyl group, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkynyl, (C) 3 -C 6 ) Cycloalkyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkylamino carbonylamino, di (C) 1 -C 4 ) Alkylamino carbonylamino group, (C) 3 -C 6 ) Cycloalkylaminocarbonylamino, (C) 1 -C 4 ) Haloalkylaminocarbonylamino, (C) 1 -C 4 ) Alkylamino carbonyl- (C) 1 -C 4 ) Alkylamino radical, di (C) 1 -C 4 ) Alkylamino carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkyl aminocarbonyl- (C) 1 -C 4 ) Alkylamino or (C) 1 -C 4 ) Haloalkylaminocarbonyl- (C) 1 -C 4 ) An alkylamino group or a dialkylamino group,
or preferably aryl, heteroaryl, cyclopentenyl or cyclohexenyl, each of which is optionally mono-or polysubstituted by identical or different substituents, wherein (in the case of heteroaryl) at least one carbonyl group may optionally be present, and the possible substituents in each case are as follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN, SF 5 Three (C) 1 -C 4 ) Alkylsilyl group, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Cycloalkyl- (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Haloalkyl- (C) 3 -C 6 ) Cycloalkyl, halo (C) 3 -C 6 ) Cycloalkyl, cyano (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Cyanoalkyl, (C) 1 -C 4 ) Hydroxyalkyl, hydroxycarbonyl- (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Alkoxycarbonyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkoxy- (C) 1 -C 4 ) Alkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Cyanoalkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Haloalkynyl group, (C) 2 -C 4 ) Cyanoalkynyl group, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Cyanoalkoxy group, (C) 1 -C 4 ) Alkoxycarbonyl- (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Alkoxyimino group, (C) 1 -C 4 ) Haloalkoxyimino group, (C) 1 -C 4 ) Alkylthio group, (C) 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 4 ) Alkylthio group, (C) 1 -C 4 ) Alkylthio- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkoxy- (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Alkylsulfinyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkylsulfonyl group, (C) 1 -C 4 ) Haloalkylsulfonyl, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 4 ) Alkylsulfonyl group, (C) 1 -C 4 ) Alkylsulfonyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkylsulfonyloxy group, (C) 1 -C 4 ) Haloalkylsulfonyloxy, (C) 1 -C 4 ) Alkylcarbonyl group, (C) 1 -C 4 ) Haloalkylcarbonyl group, (C) 1 -C 4 ) Alkylcarbonyloxy, (C) 1 -C 4 ) Alkoxycarbonyl, (C) 1 -C 4 ) Halogenated alkoxycarbonyl, aminocarbonyl, (C) 1 -C 4 ) Alkane (I) and its preparation methodAminocarbonyl group, (C) 1 -C 4 ) Halogenoalkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 2 -C 4 ) Alkenylaminocarbonyl, di (C) 2 -C 4 ) Alkenylaminocarbonyl group, (C) 3 -C 6 ) Cycloalkylaminocarbonyl group, (C) 1 -C 4 ) Alkylsulfonylamino group, (C) 1 -C 4 ) Alkylamino radical, di (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkylamino, (C) 3 -C 6 ) Cycloalkylamino, aminosulfonyl, (C) 1 -C 4 ) Alkylaminosulfonyl, di (C) 1 -C 4 ) Alkylaminosulfonyl, (C) 1 -C 4 ) Alkyl sulfoxide imino, aminothiocarbonyl, (C) 1 -C 4 ) Alkylamino thiocarbonyl, di (C) 1 -C 4 ) Alkylaminothiocarbonyl (C) 1 -C 4 ) Haloalkylaminothiocarbonyl, (C) 3 -C 6 ) Cycloalkylaminothiocarbonyl, (C) 1 -C 4 ) Alkylcarbonylamino group, (C) 1 -C 4 ) Haloalkylcarbonylamino, (C) 1 -C 4 ) Alkylcarbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Halogenoalkylcarbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylcarbonylamino group, (C) 3 -C 6 ) Cycloalkyl carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Alkylthio carbonylamino group, (C) 1 -C 4 ) Halogenoalkylthio carbonylamino, (C) 1 -C 4 ) Alkylthio carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Halogenoalkylthio carbonyl- (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylthiocarbonylamino group, (C) 3 -C 6 ) Cycloalkylthiocarbonyl- (C) 1 -C 4 ) Alkylamino, heteroaryl, oxoheteroaryl, haloheteroaryl, halooxoheteroaryl, cyanoheteroaryl, cyanooxoheteroaryl, (C) 1 -C 4 ) Haloalkyl heteroaryl or (C) 1 -C 4 ) Halogenoalkyloxohetero compoundsAn aryl group, a heteroaryl group,
x is preferably a heteroaromatic 9-or 12-membered fused bicyclic or tricyclic ring system selected from Q1 to Q12,
R 4 preferably hydrogen, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Cyanoalkyl, (C) 1 -C 4 ) Alkoxy- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkoxy- (C) 1 -C 4 ) Alkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Haloalkynyl or (C) 3 -C 6 ) A cycloalkyl group,
R 5 、R 6 each independently of the others is preferably hydrogen, cyano, halogen, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Halogenated alkynyl, (C) 3 -C 6 ) Cycloalkyl group, (C) 3 -C 6 ) Cycloalkyl- (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Haloalkyl- (C) 3 -C 6 ) Cycloalkyl, cyano (C) 3 -C 6 ) Cycloalkyl, halo (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Alkoxyimino group, (C) 1 -C 4 ) Haloalkoxyimino group, (C) 1 -C 4 ) Alkylthio group, (C) 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkylsulfonyl group, (C) 1 -C 4 ) Haloalkylsulfonyl, (C) 1 -C 4 ) Alkylsulfonyloxy, (C) 1 -C 4 ) Haloalkylsulfonyloxy, (C) 1 -C 4 ) Alkyl carbonylOr (C) 1 -C 4 ) A halogenated alkyl-carbonyl group,
n is preferably 0, 1 or 2.
In another embodiment, the invention relates to compounds of formula (I), wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 2-2, wherein R is R if X is preferably Q7 3 Not being hydrogen, halogen, cyano, nitro, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Alkylthio, (C) 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkylsulfonyl or (C) 1 -C 4 ) A haloalkylsulfonyl group.
Configuration 3-1
R 1 More preferably (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl or (C) 3 -C 6 ) A cycloalkyl group,
R 2 more preferably hydrogen and (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 3 -C 6 ) Cycloalkyl or halo (C) 3 -C 6 ) A cycloalkyl group,
R 3 more preferably hydrogen, halogen, cyano, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Haloalkylaminocarbonyl, (C) 3 -C 6 ) Cycloalkylaminocarbonyl, amino, (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkyl amino, di (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylamino, (C) 1 -C 4 ) Alkylsulfonylamino group, (C) 1 -C 4 ) Alkylcarbonylamino, (C) 1 -C 4 ) Haloalkylcarbonylamino, (C) 1 -C 4 ) Alkylcarbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkyl carbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylcarbonylamino group, (C) 3 -C 6 ) Cycloalkyl carbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Cyanoalkenyl or (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) An alkenyl group, which is a radical of an alkenyl group,
or more preferably phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, furyl, pyrazolyl, thiazolyl, oxazolyl or imidazolyl, each of which is optionally mono-or polysubstituted by identical or different substituents, where (in the case of heteroaryl) at least one carbonyl group may optionally be present and the possible substituents in each case are as follows: cyano, halogen, nitro, acetyl, hydroxy, amino, SF 5 、(C 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, halo (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Cyanoalkyl, (C) 1 -C 4 ) Hydroxyalkyl, (C) 1 -C 4 ) Alkoxy- (C) 1 -C 2 ) Alkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Cyanoalkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Halogenated alkynyl, (C) 2 -C 4 ) Cyanoalkynyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Cyanoalkoxy group, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 2 ) Alkoxy group, (C) 1 -C 4 ) Alkoxyimino group, (C) 1 -C 4 ) Haloalkoxyimino group, (C) 1 -C 4 ) Alkylthio, (C) 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkylthio- (C) 1 -C 2 ) Alkyl, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkylsulfonyl group, (C) 1 -C 4 ) Haloalkylsulfonyl, (C) 1 -C 4 ) Alkylsulfonyloxy group, (C) 1 -C 4 ) Haloalkylsulfonyloxy, (C) 1 -C 4 ) Alkylcarbonyl, (C) 1 -C 4 ) Haloalkyl carbonyl, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Halogenated alkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 3 -C 6 ) Cycloalkylaminocarbonyl, aminothiocarbonyl, (C) 1 -C 4 ) Alkylamino thiocarbonyl, di (C) 1 -C 4 ) Alkylaminothiocarbonyl (C) 1 -C 4 ) Haloalkylaminothiocarbonyl, (C) 3 -C 6 ) Cycloalkylaminothiocarbonyl, (C) 1 -C 4 ) Alkylsulfonylamino group, (C) 1 -C 4 ) Alkylamino radical, di (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkylamino, (C) 3 -C 6 ) Cycloalkylamino, aminosulfonyl, (C) 1 -C 4 ) Alkylaminosulfonyl, di (C) 1 -C 4 ) Alkylaminosulfonyl, (C) 1 -C 4 ) Alkylcarbonylamino, (C) 1 -C 4 ) Haloalkylcarbonylamino, (C) 1 -C 4 ) Alkylcarbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 1 -C 2 ) Halogenoalkylcarbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylcarbonylamino group, (C) 3 -C 6 ) Cycloalkyl carbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 1 -C 4 ) Alkylthio carbonyl amino, (C) 1 -C 4 ) Haloalkylthiocarbonylamino group, (C) 1 -C 4 ) Alkylthio carbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 1 -C 4 ) Halogenoalkylthio carbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylthiocarbonylamino or (C) 3 -C 6 ) Cycloalkanethiocarbonyl- (C) 1 -C 2 ) An alkylamino group,
x is more preferably a heteroaromatic 9-or 12-membered fused bicyclic or tricyclic ring system selected from Q1, Q2, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11 or Q12,
R 4 more preferably hydrogen and (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Halogenated alkynyl, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 4 ) Alkyl or (C) 3 -C 6 ) A cycloalkyl group,
R 5 more preferably halogen, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Halogenated alkynyl, (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Haloalkyl- (C) 3 -C 6 ) Cycloalkyl, cyano- (C) 3 -C 6 ) Cycloalkyl, halo (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Alkoxyimino group, (C) 1 -C 4 ) Haloalkoxyimino group, (C) 1 -C 4 ) Alkylthio group, (C) 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkylsulfonyl group, (C) 1 -C 4 ) Haloalkylsulfonyl, (C) 1 -C 4 ) Alkylsulfonyloxy group, (C) 1 -C 4 ) Haloalkylsulfonyloxy, (C) 1 -C 4 ) Alkylcarbonyl or (C) 1 -C 4 ) A halogenated alkyl carbonyl group,
R 6 more preferably hydrogen, cyano, halogen, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl or (C) 3 -C 6 ) A cycloalkyl group,
more preferably n is 0, 1 or 2.
In another embodiment, the invention relates to compounds of formula (I) wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 3-1, wherein R is R if X is preferably Q7 3 Is not hydrogen, halogen, cyano, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Alkoxy or (C) 1 -C 4 ) A haloalkoxy group.
Configuration 3-2
R 1 More preferably (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl or (C) 3 -C 6 ) A cycloalkyl group,
R 2 more preferably hydrogen and (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 3 -C 6 ) Cycloalkyl or halo (C) 3 -C 6 ) A cycloalkyl group, which is a cyclic alkyl group,
R 3 more preferably hydrogen, halogen, cyano, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Haloalkylaminocarbonyl group, (C) 3 -C 6 ) Cycloalkylaminocarbonyl, amino, (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkyl amino, di (C) 1 -C 4 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylamino group, (C) 1 -C 4 ) Alkylsulfonylamino group, (C) 1 -C 4 ) Alkylcarbonylamino, (C) 1 -C 4 ) Haloalkylcarbonylamino, (C) 1 -C 4 ) Alkylcarbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkyl carbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylcarbonylamino group, (C) 3 -C 6 ) Cycloalkyl carbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Cyanoalkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 2 -C 4 ) Alkynyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkynyl, (C) 3 -C 6 ) Cycloalkyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkoxycarbonyl, aminothiocarbonyl, (C) 1 -C 4 ) Alkylamino thiocarbonyl, di (C) 1 -C 4 ) Alkylaminothiocarbonyl group, (C) 1 -C 4 ) A halogenated alkyl amino thiocarbonyl group,
or more preferably phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, furyl, pyrazolyl, thiazolyl, oxazolyl, imidazolyl, pyrrolyl, cyclopentenyl or cyclohexenyl, each of which is optionally mono-or polysubstituted by identical or different substituents, wherein (in the case of heteroaryl) at least one carbonyl group may optionally be present, and the possible substituents in each case are as follows: cyano, halogen, nitro, acetyl, hydroxy, amino, SF 5 、(C 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Alkyl radical- (C) 3 -C 6 ) Cycloalkyl, halo (C) 3 -C 6 ) Cycloalkyl, cyano (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Cyanoalkyl, (C) 1 -C 4 ) Hydroxyalkyl group, (C) 1 -C 4 ) Alkoxy- (C) 1 -C 2 ) Alkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Cyanoalkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Haloalkynyl group, (C) 2 -C 4 ) Cyanoalkynyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Cyanoalkoxy group, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 2 ) Alkoxy group, (C) 1 -C 4 ) Alkoxyimino group, (C) 1 -C 4 ) Haloalkoxyimino group, (C) 1 -C 4 ) Alkylthio, (C) 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkylthio- (C) 1 -C 2 ) Alkyl, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkylsulfonyl group, (C) 1 -C 4 ) Haloalkylsulfonyl, (C) 1 -C 4 ) Alkylsulfonyloxy, (C) 1 -C 4 ) Haloalkylsulfonyloxy, (C) 1 -C 4 ) Alkylcarbonyl group, (C) 1 -C 4 ) Haloalkylcarbonyl, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Halogenoalkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 3 -C 6 ) Cycloalkylaminocarbonyl, aminothiocarbonyl, (C) 1 -C 4 ) Alkylamino thiocarbonyl, di (C) 1 -C 4 ) Alkylaminothiocarbonyl group, (C) 1 -C 4 ) Haloalkylaminothiocarbonyl, (C) 3 -C 6 ) Cycloalkylaminothiocarbonyl, (C) 1 -C 4 ) Alkylsulfonylamino group, (C) 1 -C 4 ) Alkylamino radical, di (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkylamino, (C) 3 -C 6 ) Cycloalkyl amino, aminosulfonylBase, (C) 1 -C 4 ) Alkylaminosulfonyl, di (C) 1 -C 4 ) Alkylaminosulfonyl, (C) 1 -C 4 ) Alkylcarbonylamino group, (C) 1 -C 4 ) Haloalkylcarbonylamino, (C) 1 -C 4 ) Alkylcarbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 1 -C 2 ) Haloalkyl carbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylcarbonylamino group, (C) 3 -C 6 ) Cycloalkyl carbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 1 -C 4 ) Alkylthio carbonylamino group, (C) 1 -C 4 ) Haloalkylthiocarbonylamino group, (C) 1 -C 4 ) Alkylthio carbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 1 -C 4 ) Halogenoalkylthio carbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylthiocarbonylamino or (C) 3 -C 6 ) Cycloalkanethiocarbonyl- (C) 1 -C 2 ) An alkylamino group or a dialkylamino group,
x is more preferably a heteroaromatic 9-or 12-membered fused bicyclic or tricyclic ring system selected from Q1, Q2, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11 or Q12,
R 4 more preferably hydrogen and (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Halogenated alkynyl, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 4 ) Alkyl or (C) 3 -C 6 ) A cycloalkyl group, which is a cyclic alkyl group,
R 5 more preferably halogen, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Alkynyl, (C) 2 -C 4 ) Haloalkynyl group, (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Haloalkyl- (C) 3 -C 6 ) Cycloalkyl, cyano- (C) 3 -C 6 ) Cycloalkyl, halo (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Alkoxyimino group, (C) 1 -C 4 ) Haloalkoxyimino group, (C) 1 -C 4 ) Alkylthio, (C) 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkylsulfonyl group, (C) 1 -C 4 ) Haloalkylsulfonyl, (C) 1 -C 4 ) Alkylsulfonyloxy group, (C) 1 -C 4 ) Haloalkylsulfonyloxy, (C) 1 -C 4 ) Alkylcarbonyl or (C) 1 -C 4 ) A halogenated alkyl-carbonyl group,
R 6 more preferably hydrogen, cyano, halogen, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl or (C) 3 -C 6 ) A cycloalkyl group,
more preferably n is 0, 1 or 2.
In another embodiment, the invention relates to compounds of formula (I) wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 3-2, wherein R is R if X is preferably Q7 3 Not hydrogen, halogen, cyano, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Alkoxy or (C) 1 -C 4 ) A haloalkoxy group.
Configuration 4-1
R 1 Even more preferably methyl, ethyl, n-propyl, isopropyl, cyclopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R 2 even more preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethylA tetrafluoroethyl group or a pentafluoroethyl group,
R 3 even more preferably hydrogen, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Cyanoalkenyl or (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkenyl, or even more preferably phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl, oxazolyl or imidazolyl, each of which is optionally mono-or polysubstituted by identical or different substituents and bridged to the rest of the molecule via a carbon atom, wherein the possible substituents in each case are as follows: cyano, halogen, nitro, acetyl, hydroxy, amino, (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, halo (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Cyanoalkyl, (C) 1 -C 4 ) Hydroxyalkyl group, (C) 1 -C 4 ) Alkoxy- (C) 1 -C 2 ) Alkyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 2 ) Alkoxy group, (C) 1 -C 4 ) Alkoxyimino group, (C) 1 -C 4 ) Alkylthio, (C) 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkylsulfonyl, (C) 1 -C 4 ) Haloalkylsulfonyl, (C) 1 -C 4 ) Alkylcarbonyl, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Haloalkylaminocarbonyl group, (C) 3 -C 6 ) Cycloalkylaminocarbonyl group, (C) 1 -C 4 ) Alkylsulfonylamino group, (C) 1 -C 4 ) Alkylamino radical, di (C) 1 -C 4 ) Alkane (I) and its preparation methodAlkylamino radical, (C) 1 -C 4 ) Haloalkylamino, (C) 3 -C 6 ) Cycloalkylamino group, (C) 1 -C 4 ) Alkylcarbonylamino, (C) 1 -C 4 ) Haloalkylcarbonylamino, (C) 1 -C 4 ) Alkylcarbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkyl carbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylcarbonylamino group, (C) 3 -C 6 ) Cycloalkyl carbonyl- (C) 1 -C 2 ) An alkylamino group,
x is even more preferably Q1, Q4, Q5, Q7, Q8, Q9 or Q11,
R 4 even more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxymethyl or methoxyethyl,
R 5 even more preferably fluorine, chlorine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfonyl or trifluoromethylsulfinyl,
R 6 even more preferably hydrogen, cyano, methyl, trifluoromethyl, fluorine or chlorine,
n is even more preferably 0, 1 or 2.
In another embodiment, the invention relates to compounds of formula (I) wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 4-1, wherein R is R if X is even more preferably Q7 3 Is not hydrogen, (C) 1 -C 4 ) Alkyl or (C) 1 -C 4 ) A haloalkyl group.
Configuration 4-2
R 1 Even more preferably methyl, ethyl, n-propyl, isopropyl, cyclopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R 2 even more preferablyHydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R 3 even more preferably hydrogen, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 2 -C 4 ) Alkenyl, (C) 2 -C 4 ) Haloalkenyl, (C) 2 -C 4 ) Cyanoalkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkenyl, halogen, cyano, (C) 2 -C 4 ) Alkynyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkynyl, (C) 3 -C 6 ) Cycloalkyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkoxycarbonyl, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Haloalkylaminocarbonyl, aminothiocarbonyl, (C) 1 -C 4 ) Alkylamino thiocarbonyl, di (C) 1 -C 4 ) Alkylaminothiocarbonyl group, (C) 1 -C 4 ) A haloalkylaminothiocarbonyl group,
or even more preferably phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl, oxazolyl, imidazolyl, pyrazolyl, pyrrolyl, cyclopentenyl or cyclohexenyl, each of which is optionally mono-or polysubstituted by identical or different substituents and bridged to the remainder of the molecule via a carbon atom, wherein the possible substituents in each case are as follows: cyano, halogen, nitro, acetyl, hydroxy, amino, (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, halo (C) 3 -C 6 ) Cycloalkyl, cyano (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Cyanoalkyl, (C) 1 -C 4 ) Hydroxyalkyl group, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 2 ) Alkyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) Haloalkoxy, (C) 1 -C 4 ) Alkoxy radical- (C 1 -C 2 ) Alkoxy group, (C) 1 -C 4 ) Alkoxyimino group, (C) 1 -C 4 ) Alkylthio, (C) 1 -C 4 ) Haloalkylthio, (C) 1 -C 4 ) Alkylsulfinyl (C) 1 -C 4 ) Haloalkylsulfinyl, (C) 1 -C 4 ) Alkylsulfonyl, (C) 1 -C 4 ) Haloalkylsulfonyl, (C) 1 -C 4 ) Alkylcarbonyl, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Haloalkylaminocarbonyl, (C) 3 -C 6 ) Cycloalkylaminocarbonyl group, (C) 1 -C 4 ) Alkylsulfonylamino group, (C) 1 -C 4 ) Alkylamino radical, di (C) 1 -C 4 ) Alkylamino radical, (C) 1 -C 4 ) Haloalkylamino, (C) 3 -C 6 ) Cycloalkylamino group, (C) 1 -C 4 ) Alkylcarbonylamino group, (C) 1 -C 4 ) Haloalkylcarbonylamino, (C) 1 -C 4 ) Alkylcarbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 1 -C 4 ) Halogenoalkylcarbonyl- (C) 1 -C 2 ) Alkylamino radical, (C) 3 -C 6 ) Cycloalkylcarbonylamino group, (C) 3 -C 6 ) Cycloalkyl carbonyl- (C) 1 -C 2 ) An alkylamino group or a dialkylamino group,
or even more preferably pyrazolyl or imidazolyl, each of which is optionally mono-or polysubstituted by identical or different substituents and bridged to the remainder of the molecule via a nitrogen atom, wherein the possible substituents in each case are the following: cyano, halogen, nitro, hydroxy, amino, (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) Alkoxy group, (C) 1 -C 4 ) A halogenated alkoxy group, an aminocarbonyl group,
x is even more preferably Q1, Q4, Q5, Q7, Q8, Q9, Q11 or Q12,
R 4 even more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxymethyl or methoxyethyl,
R 5 even more preferably fluorine, chlorine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfonyl or trifluoromethylsulfinyl,
R 6 even more preferably hydrogen, cyano, methyl, trifluoromethyl, fluorine or chlorine,
n is even more preferably 0, 1 or 2.
In another embodiment, the invention relates to compounds of formula (I), wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 4-2, wherein R is R if X is even more preferably Q7 3 Is not hydrogen, (C) 1 -C 4 ) Alkyl, halogen, cyano or (C) 1 -C 4 ) A haloalkyl group.
Configuration 4-3
R 1 、R 2 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 4-2, and
x is even more preferably Q1, Q7, Q8, Q9 or Q12 and
R 3 in particular hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, vinyl, isopropenyl, cyclopropylmethyl, cyclopropylethyl, cyclopropylvinyl, cyclopropylethynyl, methoxycarbonyl, ethoxycarbonyl, trifluoromethylaminocarbonyl, trifluoroethylaminocarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, aminothiocarbonyl, methylaminothiocarbonyl, dimethylaminothiocarbonyl, ethylaminothiocarbonyl,
Or is phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl, imidazolyl, pyrazolyl, pyrrolyl or cyclohexenyl, each of which is optionally mono-, di-or tri-substituted by identical or different substituents and is bridged to the remainder of the molecule via a carbon atom, wherein the possible substituents in each case are as follows: cyano, fluorine, chlorine, methyl, ethyl, isopropyl, cyclopropyl, cyanomethyl, cyanoethyl, cyanoisopropyl, cyanocyclopropyl, trifluoromethyl, trifluoroethyl, aminocarbonyl, or is pyrazolyl or imidazolyl, each of which is optionally mono-substituted with fluorine or chlorine and is bridged to the remainder of the molecule via a nitrogen atom.
In another embodiment, the invention relates to compounds of formula (I) wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 4-3, wherein R is R if X is even more preferably Q7 3 Is not hydrogen, fluoro, chloro, bromo, cyano, methyl, ethyl or isopropyl.
Configuration 5-1
R 1 The emphasis is on ethyl or isopropyl groups,
R 2 with the emphasis on methyl, ethyl or isopropyl,
R 3 with emphasis being given to hydrogen, bromine, cyano, ethenyl, cyclopropylethenyl, isopropenyl, cyclopropylethynyl, methyl, ethyl, isopropyl, cyclopropylethyl, methoxycarbonyl, trifluoroethylaminocarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, aminothiocarbonyl, methylaminothiocarbonyl, dimethylaminothiocarbonyl,
Or with emphasis is phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl (thienyl), thiazolyl, imidazolyl, pyrazolyl, pyrrolyl or cyclohexenyl, each of which is optionally mono-, di-or trisubstituted by identical or different substituents and bridged to the remainder of the molecule via a carbon atom, wherein the possible substituents in each case are as follows: cyano, fluoro, chloro, methyl, cyclopropyl, cyanomethyl, cyanoisopropyl, cyanocyclopropyl, trifluoromethyl, trifluoroethyl, aminocarbonyl,
or with emphasis is pyrazolyl or imidazolyl, each of which is optionally monosubstituted by chlorine and is bridged to the remainder of the molecule via a nitrogen atom,
x is emphasized as Q1, Q7, Q8, Q9 or Q12,
R 4 the emphasis is on the methyl group,
R 5 the emphasis is on the trifluoromethyl group,
R 6 the emphasis is on hydrogen,
n is emphasized to be 0 or 2.
In another embodiment, the invention relates to compounds of formula (I), wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 5-1, wherein R is R if X is Q7 3 Not hydrogen, bromine, cyano, methyl, ethyl or isopropyl.
Configuration 5-2
R 1 、R 2 、X、R 4 、R 5 、R 6 N has the meaning specified in configuration 5-1, and
R 3 with emphasis being given to hydrogen, bromine, cyano, ethenyl, cyclopropylethenyl, isopropenyl, cyclopropylethynyl, methyl, ethyl, isopropyl, cyclopropylethyl, methoxycarbonyl, trifluoroethylaminocarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, aminothiocarbonyl, methylaminothiocarbonyl, dimethylaminothiocarbonyl,
Or is phenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-5-yl, pyridazin-4-yl, thiophen-2-yl, thiophen-3-yl, 1, 3-thiazol-5-yl, 1H-imidazol-1-yl, 1H-imidazol-2-yl, 1H-imidazol-5-yl, 1H-pyrazol-1-yl, 1H-pyrazol-3-yl, 1H-pyrazol-4-yl, 1H-pyrazol-5-yl, 1H-pyrrol-2-yl or 1-cyclohexenyl, each of which is optionally mono-, di-or tri-substituted by identical or different substituents, wherein the possible substituents in each case are as follows: cyano, fluoro, chloro, methyl, cyclopropyl, cyanomethyl, cyanoisopropyl, cyanocyclopropyl, trifluoromethyl, trifluoroethyl, aminocarbonyl.
In another embodiment, the invention relates to compounds of formula (I) wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 5-2, wherein R is R if X is Q7 3 Is not hydrogen, bromine, cyano, methyl, ethyl or isopropyl.
Configuration 5-3
R 1 、R 2 、X、R 4 、R 5 、R 6 N has the meaning indicated in configuration 5-1, and
R 3 with emphasis being given to hydrogen, bromine, cyano, ethenyl, cyclopropylethenyl, isopropenyl, cyclopropylethynyl, methyl, ethyl, isopropyl, cyclopropylethyl, methoxycarbonyl, trifluoroethylaminocarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, aminothiocarbonyl, methylaminothiocarbonyl, dimethylaminothiocarbonyl,
Phenyl, in each case optionally monosubstituted, disubstituted or trisubstituted, identically or differently, by the following substituents: cyano, fluoro, chloro, methyl, cyanomethyl, cyanoisopropyl, cyanocyclopropyl, trifluoromethyl or aminocarbonyl,
pyridin-2-yl, pyridin-3-yl or pyridin-4-yl, each of which is optionally mono-substituted by fluorine or chlorine,
(ii) a pyrimidin-5-yl group,
(ii) a pyridazin-4-yl group,
thien-2-yl or thien-3-yl, each of which is optionally mono-or disubstituted by chlorine,
1, 3-thiazol-5-yl, optionally mono-substituted with methyl,
1H-imidazol-1-yl, 1H-imidazol-2-yl, or 1H-imidazol-5-yl, each optionally mono-or di-substituted with chlorine or methyl,
1H-pyrazol-1-yl, 1H-pyrazol-3-yl, 1H-pyrazol-4-yl or 1H-pyrazol-5-yl, each of which is optionally mono-, di-or tri-substituted, identically or differently, with: chlorine, methyl, cyclopropyl, trifluoromethyl or trifluoroethyl,
1H-pyrrol-2-yl, in each case optionally mono-or disubstituted identically or differently by methyl or cyano,
1-cyclohexenyl which is in each case optionally monosubstituted or disubstituted, identically or differently, by methyl or trifluoromethyl.
In another embodiment, the invention relates to compounds of formula (I) wherein X, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration 5-3, wherein if X is Q7, then R 3 Not hydrogen, bromine, cyano, methyl, ethyl or isopropyl.
If R is 3 In the case of substituted heteroaryl groups, the substitution on the heteroaryl group can be effected by substituting hydrogen on carbon and/or nitrogen atoms.
In a preferred embodiment, the invention relates to compounds of formula (I) wherein X is Q1 and R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3).
In a preferred embodiment, the invention relates to compounds of formula (I) wherein X is Q1, R 4 Is methyl, R 5 Is trifluoromethyl, R 6 Is hydrogen, and R 1 、R 2 、R 3 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3).
In a preferred embodiment, the invention relates to compounds of formula (I) wherein X is Q7, and R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3).
In the preferredIn an embodiment, the invention relates to compounds of formula (I) wherein X is Q7, R 4 Is methyl, R 5 Is trifluoromethyl, R 6 Is hydrogen, and R 1 、R 2 、R 3 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3).
In a preferred embodiment, the invention relates to compounds of formula (I) wherein X is Q8, and R is 1 、R 2 、R 3 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3).
In a preferred embodiment, the invention relates to compounds of formula (I) wherein X is Q8, R 5 Is trifluoromethyl, R 6 Is hydrogen, and R 1 、R 2 、R 3 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3).
In a preferred embodiment, the invention relates to compounds of formula (I) wherein X is Q9, and R is 1 、R 2 、R 3 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3).
In a preferred embodiment, the invention relates to compounds of formula (I) wherein X is Q9, R 5 Is trifluoromethyl, R 6 Is hydrogen, and R 1 、R 2 、R 3 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3).
In the preferred aspectsIn an embodiment of (I), the invention relates to compounds of formula (I), wherein X is Q12, and R is 1 、R 2 、R 3 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3).
In a preferred embodiment, the invention relates to compounds of formula (I) wherein X is Q12, R 5 Is trifluoromethyl, R 6 Is hydrogen, and R 1 、R 2 、R 3 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3).
In a preferred embodiment, the invention relates to compounds of formula (I) wherein X is Q1, Q7, Q8, Q9 or Q12, and R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3).
In a preferred embodiment, the invention relates to compounds of formula (I) wherein X is Q1, Q8, Q9 or Q12, and R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3).
In a preferred embodiment, the invention relates to compounds of formula (I), wherein R 1 、R 2 、X、R 4 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3), and R 3 Having the structure specified in configuration (5-1)Meaning.
In a preferred embodiment, the invention relates to compounds of formula (I), wherein R 1 、R 2 、X、R 4 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3), and R has the meaning specified in 3 Has the meaning specified in configuration (5-2).
In a preferred embodiment, the invention relates to compounds of formula (I), wherein R 1 、R 2 、X、R 4 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3), and R has the meaning specified in 3 Has the meaning specified in configuration (5-3).
In a preferred embodiment, the invention relates to compounds of formula (I), wherein R 1 、R 2 、X、R 4 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3), and
R 3 is hydrogen, bromo, cyano, ethenyl, cyclopropylethenyl, isopropenyl, cyclopropylethynyl, methyl, ethyl, isopropyl, cyclopropylethyl, methoxycarbonyl, trifluoroethylaminocarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, aminothiocarbonyl, methylaminothiocarbonyl or dimethylaminothiocarbonyl.
In a preferred embodiment, the invention relates to compounds of formula (I), wherein R 1 、R 2 、X、R 4 、R 5 、R 6 And n has the content specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3)Am, and
R 3 is phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl (thienyl), thiazolyl, imidazolyl, pyrazolyl, pyrrolyl or cyclohexenyl, each of which is optionally mono-, di-or tri-substituted by identical or different substituents and is bridged to the remainder of the molecule via a carbon atom, wherein the possible substituents in each case are as follows: cyano, fluoro, chloro, methyl, cyclopropyl, cyanomethyl, cyanoisopropyl, cyanocyclopropyl, trifluoromethyl, trifluoroethyl, aminocarbonyl.
In a preferred embodiment, the invention relates to compounds of formula (I), wherein R 1 、R 2 、X、R 4 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3), and
r3 is pyrazolyl or imidazolyl, each of which is optionally mono-substituted with chlorine and bridged to the rest of the molecule via a nitrogen atom.
In a preferred embodiment, the invention relates to compounds of formula (I), wherein R 2 、R 3 、X、R 4 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3), and R has the meaning specified in 1 Is an ethyl group.
In a preferred embodiment, the invention relates to compounds of formula (I), wherein R 2 、R 3 、X、R 4 、R 5 、R 6 And n has the meaning specified in configuration (1-1) or configuration (1-2) or configuration (2-1) or configuration (2-2) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (4-3) or configuration (5-1) or configuration (5-2) or configuration (5-3), and R has the meaning specified in 1 Is an isopropyl group.
In the definitions listed generally or within the preferred ranges, unless otherwise indicated, halogen is selected from fluorine, chlorine, bromine and iodine, preferably from fluorine, chlorine and bromine.
Aryl (including as part of a larger unit such as arylalkyl) unless otherwise defined, is selected from phenyl, naphthyl, anthryl, phenanthryl, and preferably phenyl;
in the context of the present invention, unless defined differently, the term "alkyl", by itself or in combination with other terms (for example haloalkyl), is understood to mean a radical of a saturated aliphatic hydrocarbon group having from 1 to 12 carbon atoms, which may be branched or unbranched. C 1 -C 12 Examples of-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1, 2-dimethylpropyl, hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl. Among these alkyl groups, C is particularly preferred 1 -C 6 -an alkyl group. Particularly preferred is C 1 -C 4 -an alkyl group.
According to the invention, unless defined differently otherwise, the term "alkenyl", by itself or in combination with other terms, should be understood to mean a straight-chain or branched C having at least one double bond 2 -C 12 Alkenyl groups, such as vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1, 3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1, 4-hexadienyl. Among these groups, C is preferred 2 -C 6 Alkenyl and particularly preferably C 2 -C 4 -an alkenyl group.
According to the invention, unless defined differently, the term "alkynyl", by itself or in combination with other terms, should be understood as meaning a straight-chain or branched C having at least one triple bond 2 -C 12 Alkynyl radicals, such as the ethynyl, 1-propynyl and propargyl radicals. Among these groups, C is preferred 3 -C 6 Alkynyl and particularly preferably C 3 -C 4 -alkynyl. Alkynyl groups may also contain at least one double bond.
According to the invention, unless otherwise defined differently, the term "cycloalkyl", by itself or in combination with other terms, should be understood to mean C 3 -C 8 Cycloalkyl radicals, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Among these groups, C is preferred 3 -C 6 -a cycloalkyl group.
In the present invention, the term "alkoxy", by itself or in combination with other terms (e.g. haloalkoxy), is to be understood as meaning an O-alkyl group, wherein the term "alkyl" is as defined above.
Halogen-substituted groups such as haloalkyl are monohalogenated or polyhalogenated up to the maximum number of possible substituents. In the case of polyhalogenation, the halogen atoms can be identical or different. Halogen here is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
Unless otherwise indicated, an optionally substituted group may be mono-or polysubstituted, wherein in the case of polysubstitution the substituents may be the same or different.
The radical definitions or explanations given above in general terms or listed within preferred ranges apply correspondingly to the end products as well as to the starting materials and intermediates. These group definitions may be combined with each other as desired, i.e., including combinations between the respective preferred ranges.
Preference is given according to the invention to the use of compounds of the formula (I) which contain a combination of the preferred meanings listed above.
Particular preference is given according to the invention to the use of compounds of the formula (I) which contain a combination of the particularly preferred meanings listed above.
Very particular preference is given according to the invention to the use of compounds of the formula (I) which comprise a combination of the very particularly preferred meanings listed above.
Most preferred according to the invention are the compounds of formula (I) comprising combinations of the most preferred meanings listed above.
Depending on the nature of the substituents, the compounds of the formula (I) may be in the form of geometric and/or optical isomers or mixtures of corresponding isomers of different composition. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Thus, the present invention includes both the pure stereoisomers and any desired mixtures of these isomers.
The compounds of formula (I) of the present invention can be obtained by the process shown in the following scheme:
method A
The preparation of compounds of formula (I) wherein R is described below 3 A general method for aryl, heteroaryl, cyclopentenyl or cyclohexenyl (optionally substituted as described above) and X is Q1, Q2, Q3, Q7 or Q10, for example by means of a compound of formula (I) wherein X is Q1, Q2 or Q3.
Figure GDA0003969167050000321
Radical R 1 、R 2 、R 3 、R 5 And R 6 Have the above-mentioned meanings. A is-N-R 4 O or S, wherein R 4 Have the above-mentioned meanings. X 1 And X 2 Is halogen. R 7 Is (C) 1 -C 4 ) An alkyl group.
Step a)
The compound of formula (III) may be prepared from the imidazole derivative of formula (II), for example by reaction with a halogenating agent such as N-bromosuccinimide (NBS) in a solvent such as tetrahydrofuran, or by reaction of the compound of formula (II) with NBS and azobis (isobutyronitrile) (AIBN) in tetrachloromethane or chloroform, similar to the processes described in, for example, WO2013/149997, WO2014/115077 or WO 2011/123609.
The imidazole derivatives of formula (II) may be commercially available or may be prepared by known methods, for example similar to the methods described in WO2014/191894, US2003/229079 or WO 2013/156608.
Step b)
A compound of formula (III) — wherein X 1 Preferably halogen selected from chlorine or bromine, to compounds of formula (IV), e.g. by means of transition metalsMediated cross-coupling [ see chem. Rev.1995,95,2457-2483; tetrahedron 2002,58,9633-9695; metal-Catalyzed Cross-Coupling Reactions (ed.: A. De Meijere, F. Diederich), 2 nd edition, wiley-VCH, weinheim,2004]Or by nucleophilic aromatic substitution (see methods described in Bioorganic and Medicinal Chemistry Letters 2007,17,5825-5830 or US 4125726).
For example, according to known processes (see WO2012/143599, US2014/94474, US2014/243316, US2015/284358 or Journal of Organic Chemistry 2004,69, 8829-8835), in the presence of a suitable catalyst selected from transition metal salts, where X can be reacted with a base in the presence of a base catalyst selected from the group consisting of the transition metal salts 1 Preferably chlorine or bromine, with a suitable boronic acid [ R ] 3 -B(OH) 2 ]Or a borate ester reaction to give a compound of formula (IV). Examples of preferred coupling catalysts include palladium catalysts, such as [1,1' -bis (diphenylphosphino) ferrocene]Palladium (II) dichloride, bis (triphenylphosphine) palladium (II) dichloride or tetrakis (triphenylphosphine) palladium. Suitable basic reaction assistants for carrying out the process are preferably sodium carbonate, potassium carbonate or cesium carbonate. Desired boronic acid derivatives [ R 3 -B(OH) 2 ]Or Boronic ester derivatives are known and/or commercially available, or they can be prepared by generally known methods (see Boronic Acids (ed.g. d.hall), 2 nd edition, wiley-VCH, weinheim, 2011). In this case, the reaction is preferably carried out in a mixture of water and an organic solvent selected from conventional organic solvents which are inert under the reaction conditions. Ethers such as tetrahydrofuran, dioxane or 1, 2-dimethoxyethane are generally used.
Alternatively, stannane derivatives [ R ] may be used 3 -Sn(Et) 4 ]As coupling partner (see US2013/281433, WO2004/99177 or WO 2016/71214). Desired stannane derivatives [ R 3 -Sn(Et) 4 ]Are known and/or commercially available, or they can be prepared by generally known methods (see WO2016/71214 or WO 2007/1480930).
Coupling of halogenated imidazole derivatives of formula (III) with NH-containing heteroaromatic compounds, such as imidazole or pyrazole (optionally substituted as described above) to give compounds of formula (IV)Under basic conditions (for example by means of sodium hydride in dimethylformamide, see WO 2005/58898). Alternatively, the reaction may be carried out by catalysis with a copper salt (I), such as copper (I) iodide, in the presence of a suitable ligand, such as (trans) -N, N' -dimethylcyclohexane-1, 2-diamine or R- (+) -proline, and a suitable base, such as potassium carbonate or phosphate, in a suitable solvent, such as 1, 4-dioxane or toluene, under an inert atmosphere (see, for example, WO 2016/109559). Under these reaction conditions, R may also be formed 3 A compound of formula (IV) of = H.
Step c)
Imidazole derivatives of formula (V) < CHEM > - < CHEM > wherein X 2 Preferably a halogen selected from bromine or iodine-can be prepared from compounds of formula (IV) by reaction with, for example, bromine or N-bromosuccinimide (NBS) (see WO2009/115572 or WO 2010/91411) or N-iodosuccinimide (NIS), optionally in the presence of acetic acid or trifluoroacetic acid (see WO2008/63287, WO2007/87548 or WO 2009/152025), using standard methods.
Step d)
A compound of formula (V) — wherein X 2 Preferably a halogen selected from bromine or iodine, into a compound of formula (VI), for example by reaction with a thiol derivative (R) under basic conditions 1 -SH) and a copper (I) salt (see EP257918 or WO 2009/152025), or by nucleophilic aromatic substitution (see Australian Journal of Chemistry 1987,40, 1415-1425).
Or, a compound of formula (V) — wherein X 2 Preferably halogen selected from bromine or iodine, with thiol derivatives (R) 1 -SH) can be carried out over a palladium catalyst such as tris (dibenzylideneacetone) dipalladium [ Pd 2 (dba) 3 ]In the presence of oxygen. In this case, amine bases such as triethylamine or N, N-Diisopropylethylamine (DIPEA) and phosphine ligands such as Xantphos (see WO2013/25958, WO2013/66869, US2009/27039, WO2011/58149, WO2011/143466 or Bioorganic and Medicinal Chemistry Letters 2016,26, 2984-2987) are generally used. In this case, the reaction is preferably carried out in a solvent selected from conventional organic solvents which are inert under the reaction conditions. Ethers are preferred, e.g. Dioxane or 1, 2-dimethoxyethane.
Thiol derivatives, such as methanethiol, ethanethiol or isopropylthiol, are commercially available or can be prepared by known methods, for example analogously to the methods described in US2006/25633, US2006/111591, US2820062, chemical Communications,13 (2000), 1163-1164 or Journal of the American Chemical Society,44 (1922), pages 1323-1333.
Step e)
The esters of formula (VI) can be converted to carboxylic acids of formula (VII) using standard methods (see, e.g., WO2014/191894, US2006/194779, WO2014/86663 or European Journal of Organic Chemistry,2009, 213-222), for example using an alkali metal hydroxide such as sodium hydroxide or lithium hydroxide as a base in an alcohol such as methanol or ethanol as a solvent.
Step f)
The compound of formula (I, n = 0) may be prepared from a compound of formula (VII) and a compound of formula (VIII) in the presence of a condensation component.
The compounds of formula (VIII) may be commercially available or may be prepared by known methods, for example similar to the methods described in WO 2010/125985, WO 2012/074135, WO 2012/086848, WO 2013/018928, WO 2015/000715, WO 2015/121136, WO2016/039441, WO2016/059145, WO2016/071214, WO 2016/169882, WO 2016/169886 or WO 2016/124557.
The conversion of the compound of formula (I, n = 0) may be carried out without or in a solvent, preferably in a solvent selected from conventional solvents which are inert under the reaction conditions. Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; alcohols, such as methanol, ethanol or isopropanol; nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone; or a nitrogen-containing compound such as pyridine.
Examples of suitable condensation components are carbodiimides, such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1, 3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride, or a mixture of triphenylphosphine and an azo diester such as diethyl azodicarboxylate (dimethylazodicarboxylic acid).
The reaction may be carried out in the presence of a suitable catalyst, for example 1-hydroxybenzotriazole.
The reaction may be carried out in the presence of an acid or a base.
Examples of acids that can be used in the reaction are sulfonic acids such as methanesulfonic acid or p-toluenesulfonic acid; carboxylic acids, such as acetic acid; or polyphosphoric acid.
Examples of suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2, 6-lutidine, 1, 8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
Step g)
Compounds of formula (I, n =1 or 2) may be prepared by oxidation of a compound of formula (I, n = 0), for example in analogy to the process described in WO 2016/169882 or WO 2016/124557. The oxidation is usually carried out in a solvent. Preferably halogenated hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; alcohols, such as methanol or ethanol; formic acid, acetic acid, propionic acid or water.
Examples of suitable oxidizing components are hydrogen peroxide and m-chloroperoxybenzoic acid.
Method B
General methods for the preparation of compounds of formula (I) wherein X is Q4, Q5 or Q6 are described below, for example with reference to compounds of formula (I) wherein X is Q5.
Figure GDA0003969167050000361
Radical R 1 、R 2 、R 3 、R 5 And R 6 Have the above-mentioned meanings. X 3 Is halogen.
Step a)
The carboxylic acids of the formula (VII) can be converted in analogy to the processes described in U.S. Pat. No. 4,08905 or Organic Letters,2009,11 1023-1026, in the presence of N, O-dimethylhydroxylamine hydrochloride in the presence of a condensation component into the Weinreb amides of the formula (IX).
The conversion of the compound of formula (IX) is preferably carried out in a solvent selected from conventional solvents which are inert under the reaction conditions. Preferably nitriles, such as acetonitrile or propionitrile; or aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone.
Examples of suitable condensation components are carbodiimides, such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) and 1, 3-dicyclohexylcarbodiimide; anhydrides, for example acetic anhydride and trifluoroacetic anhydride or isobutyl chloroformate.
The reaction can be carried out in the presence of a base such as triethylamine or N-methylmorpholine.
Step b)
Weinreb amides of formula (IX) can be converted to ketones of formula (X) in the presence of methyllithium or a methylmagnesium halide, such as methylmagnesium bromide, analogously to the process described in Journal of Medicinal Chemistry,1995,38,4972-4975 or Organic Letters,2012,14 6158-6161.
The conversion of the compound of formula (X) is carried out in a solvent selected from conventional solvents which are inert under the reaction conditions. Ethers, such as tetrahydrofuran or diethyl ether, are preferred.
Step c)
The ketone of formula (X) can be converted to the enolate (enolate) by deprotonation using Lithium Diisopropylamide (LDA) in tetrahydrofuran in analogy to the procedure described in Chemistry-A European Journal 2011,17, 4839-4848. The enolate formed can then be converted into a silyl enol ether, for example using trimethylchlorosilane (TMSCl), and subsequently converted into a compound of formula (XI) by alpha-halogenation, for example using N-bromosuccinimide (NBS). Alternatively, starting from the ketone of formula (X), it is also possible to use other known processes in the literature for α -halogenation, for example analogously to the processes described in US2006/52378, WO2005/7631, US2012/214791 or US 4544664.
Step d)
Compounds of formula (I, n = 0) may be prepared by cyclizing a compound of formula (XI) with an amine of formula (XII). The cyclisation is carried out by known methods, for example in ethanol, acetonitrile or N, N-dimethylformamide, analogously to the methods described in, for example, WO2005/66177, WO2012/88411, WO2013/3298, US2009/203705, US2012/258951, WO2012/168733, WO2014/187762 or j.med.chem.1988 31 1590-1595.
The compounds of formula (XII) are commercially available or can be prepared by known methods, for example analogously to the methods described in US2009/170849, WO2016/51193, WO2016/107742 or WO 2016/71214.
Step e)
Analogously to process a, step g), the compound of formula (I, n = 0) is converted into a compound of formula (I, n =1 or 2).
Method C
General methods for preparing compounds of formula (I) wherein X is Q8, Q9, Q11 or Q12 are described below, for example with reference to compounds of formula (I) wherein X is Q8.
Figure GDA0003969167050000381
Radical R 1 、R 2 、R 3 、R 5 And R 6 Have the above-mentioned meanings. X 4 And X 5 Is halogen.
The order of steps b) to e) may be changed from one another.
Step a)
Analogously to process A, steps a) and c), imidazole derivatives of formula (XIII) may be reacted with halogenating agents such as NBS, bromine or iodine to give compounds of formula (XIV) — wherein X 4 And X 5 Preferably a halogen selected from bromine or iodine (see WO2011/85269, WO2004/80998 or WO 2016/87487).
The compounds of formula (XIII) are commercially available or may be prepared by known methods, for example similar to those described in Advanced Synthesis and Catalysis 2009,351,2912-2920, synthetic Communications1989,19,2551-2566 or WO 2009/27746.
Step b)
The compound of formula (XVI) can be synthesized from the compound of formula (XIV) by reaction with the compound of formula (XV), for example by reaction under basic conditions, for example by using carbonate bases such as sodium carbonate or lithium carbonate, in aprotic polar solvents such as N, N-dimethylformamide, similar to the methods described in Bioorganic and Medicinal Chemistry 2008,16,9524-9535, bioorganic and Medicinal Chemistry Letters 1997,7,2723-2728 or WO 2016/20286.
Alternatively, the reaction may be carried out in the presence of copper or copper (I) iodide and a basic reaction promoter such as trans-N, N' -dimethylcyclohexane-1, 2-diamine, potassium carbonate or potassium phosphate in a suitable solvent or diluent, for example in analogy to the methods described in WO2016/20286 or KR 2015/66012. Useful solvents or diluents include all inert organic solvents, such as aliphatic or aromatic hydrocarbons. Toluene is preferably used.
The compounds of formula (XV) are commercially available or can be prepared by known methods, for example, similar to those described in Organic Letters 2011,13, 3542-3545.
Step c)
Compounds comprising a leaving group (R) are prepared by reaction with an electrophile, a compound comprising a leaving group (R) using standard methods (see, e.g., heterocycles 1999,50,1081-1090, WO2009/70045 or Bioorganic and Medicinal Chemistry Letters 2007,17,1369-1375 2 -LG; LG = chloro, bromo, iodo, O-trifluoromethanesulfonate, O-methanesulfonyl), the imidazole derivative of formula (XVI) can be converted into an N-substituted imidazole derivative of formula (XVII) using, for example, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide as a base in an alcohol such as ethanol as a solvent.
Step d)
Analogously to process a, step d), a compound of formula (XVII) is converted into a compound of formula (I, n = 0).
Step e)
Analogously to process a, step g), the compound of formula (I, n = 0) is converted into a compound of formula (I, n =1 or 2).
Method D
General methods for the preparation of compounds of formula (I) wherein X is Q8, Q9, Q11 or Q12 are described below, for example with reference to compounds of formula (I) wherein X is Q8.
Figure GDA0003969167050000391
Radical R 1 、R 2 、R 3 、R 5 And R 6 Have the above-mentioned meanings. Boc = tert-butoxycarbonyl group
Step a)
Imidazole derivatives of formula (XVIII) can be prepared by known methods from compounds of formula (VII) by reaction with Diphenylphosphorylazide (DPPA) in tert-butanol in the presence of an amine base such as triethylamine, for example analogously to the methods described in US2012/149699, WO2011/112766 or WO 2009/23179.
Step b)
The N-Boc-protected imidazole derivative of formula (XVIII) can be converted to an imidazole derivative of formula (XIX) using standard methods (see, e.g., WO2015/166289, US2008/9497, or WO 2006/77424) by using an acid, such as hydrochloric acid or trifluoroacetic acid, in a solvent such as 1, 4-dioxane or methanol.
Step c)
Imidazole derivatives of formula (XIX) may be converted to compounds of formula (I, n = 0) by imine formation (e.g. in toluene or dichloromethane) by reaction with compounds of formula (XX) and subsequent cyclization optionally using an acid such as titanium tetrachloride or titanium isopropoxide, for example analogously to the process described in WO2012/66061 or Bioorganic and Medicinal Chemistry Letters 2017,27, 1593-1597.
The compounds of formula (XX) can be prepared analogously to methods known in the literature (see, for example, WO2015/116882, WO2017/75694, angewandte Chemie International Edition 2011,50,1702-1706 or Organic Letters 2010,12, 2884-2887).
Step d)
Analogously to process a, step g), the compound of formula (I, n = 0) is converted into a compound of formula (I, n =1 or 2).
Method E
General methods for the preparation of compounds of formula (I) wherein X is Q1, Q2, Q3, Q7 or Q10 are described below, for example with reference to compounds of formula (I) wherein X is Q1, Q2 or Q3.
Figure GDA0003969167050000411
Radical R 1 、R 2 、R 3 、R 5 And R 6 Have the above-mentioned meanings. A is-N-R 4 O or S, wherein R 4 Have the above-mentioned meanings. X 1 Is halogen. R 7 Is (C) 1 -C 4 ) An alkyl group.
Step a)
The compound of formula (III) may be prepared from an imidazole derivative of formula (II), for example by reaction with a halogenating agent such as N-bromosuccinimide (NBS) in a solvent such as tetrahydrofuran, or by reaction of a compound of formula (II) with NBS and azobis (isobutyronitrile) (AIBN) in tetrachloromethane or chloroform, for example similar to the process described in WO2013/149997, WO2014/115077 or WO 2011/123609.
The imidazole derivatives of formula (II) may be commercially available or may be prepared by known methods, for example similar to the methods described in WO2014/191894, US2003/229079 or WO 2013/156608.
Step b)
Imidazole derivatives of formula (XXI) can be prepared from compounds of formula (III) by reaction with disulfides (R) using standard procedures 1 -S-S-R 1 ) And for example strong bases, preferably Lithium Diisopropylamide (LDA) (in tetrahydrofuran) (see Bioorganic and Medicinal Chemistry Letters 2010,20, 1084-108) or for example hydrogen peroxide and iodine (in ethanol) (see Synthesis 2015,47, 659-671).
Step c)
In analogy to process A, step e), a compound of the formula (XXI) is converted into a compound of the formula (XXII).
Step d)
In analogy to process A, step f), a compound of formula (XXII) is reacted with a compound of formula (VIII) to give a compound of formula (Ia, X) 1 ＝R 3 = halogen, n = 0).
Step e, h)
The conversion of the compound of formula (I-a, n = 0) to the compound of formula (I-a, n =1 or 2) and the conversion of the compound of formula (I, n = 0) to the compound of formula (I, n =1 or 2) is carried out analogously to step g) of method a.
Step f, g)
The conversion of the compound of formula (I-a, n = 0) to the compound of formula (I, n = 0) and the conversion of the compound of formula (I-a, n =1 or 2) to the compound of formula (I, n =1 or 2) is carried out analogously to step b) of method a.
Starting from compounds of the formula (XXII), compounds of the formula (I) can also be prepared analogously to process B and subsequently to steps E) - > f) or g) - > h) of process E, where X is Q4, Q5 or Q6.
Method F
The following describes the preparation of compounds wherein R 3 The general process for compounds of formula (I) which are functional groups as exemplified above is described, for example, with reference to compounds of formula (I) wherein X is Q1, Q2 or Q3.
Figure GDA0003969167050000431
Radical R 1 、R 2 、R 5 And R 6 Have the above-mentioned meanings. A is-N-R 4 O or S, wherein R 4 Have the above-mentioned meanings. X 1 Is halogen. R is 7 Is (C) 1 -C 4 ) An alkyl group. n is 0, 1 or 2.
Step a)
According to methods known from the literature, compounds of formula (I-b) can be prepared from compounds of formula (I-a) by reaction with carbon monoxide, for example by reaction in a suitable alcohol (e.g. methanol or ethanol) in the presence of a phosphine ligand such as triphenylphosphine, xantphos [ (4, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene) ] or BINAP [2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ], in the presence of a palladium catalyst such as palladium (II) dichloride, tetrakis (triphenylphosphine) palladium or bis (acetonitrile) palladium (II) dichloride, and optionally in the presence of a suitable base such as triethylamine [ see, for example, US2014/46072, WO2004/106293 or Journal of Medicinal Chemistry 2009,52,2880-2898].
Step b)
The resulting ester of formula (I-b) can be converted to the corresponding amide of formula (I-c), for example by saponification in analogy to step e) of process a and subsequent carboxylic acid activation by a coupling agent such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) [ see also step f of process a) ] or by conversion to an acid chloride and reaction with an amine [ see, for example, WO2012/146666, US2014/315924 or WO2005/4863].
Amide formation can be accomplished directly from the ester of formula (I-b) by reaction with an amine, for example in methanol [ see, e.g., WO2014/72261 or US2013/338137], optionally in the presence of a base such as lithium bis (trimethylsilyl) amide (LHMDS) [ see, e.g., WO2016/87487 ].
Step c)
Thioamides of formula (I-d) can be prepared from amides of formula (I-c) by reaction with a suitable sulfurizing agent, for example a Lawson reagent (see, analogously, for example WO 2005/9435) or P4S10 (see, analogously, for example European Journal of Medicinal Chemistry 1995 30, 915-924) in a suitable solvent, for example toluene or xylene.
Step d)
The compound of formula (I-e) may be represented by the formula [ I-c, R 3 ＝-C(O)NH 2 ]By reaction with a suitable condensing component (e.g. phosphorus oxychloride (POCl), optionally in a suitable solvent such as dimethylformamide or toluene 3 ) Or phosphorus pentachloride (PCl) 5 ) Reacted to prepare (see, similarly, e.g., US2013/338137, WO2005/77950, WO 2007/123516); or in a suitable solvent such as dichloromethane, tetrahydrofuran or pyridine andoptionally by trifluoroacetic anhydride in the presence of a base such as triethylamine (see, analogously, e.g., WO2014/198853 or Bioorganic and Medicinal Chemistry Letters 2011,21, 6515-6518).
Step e)
Analogously to step b) of A), the compound of formula (I-a) is converted into the compound of formula (I-f).
Step f)
Compounds of formula (I-g) can be prepared from compounds of formula (I-f) in a solvent such as ethyl acetate or methanol by using a hydrogenation catalyst such as palladium on carbon or platinum dioxide and reacting with hydrogen using standard methods (see US2008/318935, US2011/275801 or WO 2015/91584).
Step g)
Analogously to process A, step b), the compounds of the formula (I-a) can be converted into compounds of the formula (I-f).
Alternatively, the reaction can be carried out in a suitable solvent such as dimethylformamide, by using a terminal alkyne derivative, a palladium catalyst such as bis (triphenylphosphine) palladium (II) dichloride or tetrakis (triphenylphosphine) palladium, cuprous iodide and an amine base such as triethylamine (see, analogously, e.g. WO 2002046166 or Organic & Biomolecular Chemistry 2011,9, 450-462).
Method and use
The invention also relates to a method for controlling animal pests, in which compounds of the formula (I) can be acted on the animal pests and/or their habitat. The control of animal pests is preferably carried out in agriculture and forestry and in material protection. This preferably excludes methods for surgical or therapeutic treatment of the human or animal body as well as diagnostic methods carried out on the human or animal body.
The invention also relates to the use of the compounds of formula (I) as pesticides, in particular as crop protection compositions.
In the context of the present application, the term "pesticide" also always includes the term "crop protection composition" in each case.
In view of good plant tolerance, favourable warm-blooded animal toxicity and good environmental compatibility, the compounds of the formula (I) are suitable for protecting plants and plant organs against biotic and abiotic stress factors, for increasing the recovery efficiency, for improving the quality of harvested materials and for controlling animal pests, in particular insects, arachnids, helminths, especially nematodes and molluscs, encountered in agriculture, horticulture, animal husbandry, aquaculture, forestry, garden and leisure facilities, the protection of stored products and materials and in the hygiene field.
In the context of the present patent application, the term "hygiene" is understood to mean any and all measures, devices and methods intended to prevent diseases, in particular infectious diseases, and for protecting the health of humans and animals and/or for protecting the environment and/or for keeping clean. According to the invention, this includes, inter alia, measures for cleaning, disinfecting and sterilizing, for example, textiles or hard surfaces, in particular surfaces made of glass, wood, cement, porcelain, ceramic, plastic or metal, in order to ensure that these surfaces are free from hygiene pests and/or their secretions. In this regard, the scope of protection of the present invention preferably excludes surgical or therapeutic treatment methods applied to the human or animal body, as well as diagnostic methods performed on the human or animal body.
The term "hygiene field" covers all areas, technical fields and industrial applications where these hygiene measures, apparatuses and methods are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, hospitals, stables, animal husbandry and the like.
The term "sanitary pest" is therefore understood to mean one or more animal pests whose presence in the hygiene field is problematic, especially for health reasons. The main objective is therefore to avoid the presence and/or contact with sanitary pests in the hygiene sector or to limit the presence and/or contact with sanitary pests in the hygiene sector to a minimum. This can be achieved in particular by using pesticides which can be used both for preventing infections and for preventing existing infections. Agents that prevent or reduce contact with pests may also be used. Sanitary pests include, for example, the organisms mentioned hereinafter.
Thus, the term "sanitary protection" includes all actions to maintain and/or improve these sanitary measures, devices, and methods.
The compounds of the formula (I) can preferably be used as pesticides. It is active against normally sensitive and resistant species and against all or a specific developmental stage. The pests include:
Pests from the phylum Arthropoda (Arthropoda), in particular from the class Arachnida (Arachnida), such as Dermatophagoides (Acarus spp.), such as Dermatophagoides pteronyssinus (Acarus sriro), lycium barbarum (Aceria kuko), terminalia citrinum (Aceria sheldoni), dermanyssus (Aculops spp.), phymatopsis (Aculus spp.), such as Dermanyssus formosanus (Aculus focusfocusfocuskui), dermanyssus Malayanus (Aculus schlechleri), oryza sativa (Amblyomma spp.), tetranychus cratus (Amanisthus viennensis), oryza rufoenii (Argas spp.), buxus (Boletus spp.), breynia brachypus (Breynebacteria spyprus spp.), such as Breviporhinus gracilis (Bryphus spp.), paecies sporus spp.), and Acarus bipolaris (Acanthopanax spp.), such as Breynia graciliaris sp.), dermatophagoides (Chloropeptos spp.), dermanyssus gallinae (Glacina), dermatophagoides (Dermatophagoides pteronyssinus), dermatophagoides (Dermatophagoides farinae), dermacentor spp.), oreophytes (Eotophyllus spp.), e.g. Eotophyllus tricorae, oetiphytes pyris (Epitrimerus pyrifera), euptes (Eutetranychus spp.), e.g. Eutetranychus basksi, oesophagus (Eriophysteris spp.), e.g. Pyricularis (Eriophagus pyrus pyris), glycyrrhinus (Glychagus durius), dermatophagoides (Haliotides fortunei), euonymus fortunei (Haliotrophus fasciatus spp.), hemis semisolenopsis (Hylotoides pteronyssimus spp.), e.e.g. Polyleptus manges (Hymenotrophae), hard tick (Ixodes spp.), cochasmys sp., latridectus spp., orchis spp., olipomyces spp., such as Peganpinus coffei (Oligonychus coffei), oligonychus conformus (Oligonychus conformus), acanthopanax gracilis (Oligonychus ilicus), acanthopanax canus (Oligonychus nitis), acanthopanax canus (Oligonychus fasciatus), acanthopanax gracilistylus (Oligonychus mangiferus), acanthopanax gracilis (Oligonychus mangus), acanthopanax gracilis (Oligonychus pratensis), acanthopanax gracilis (Oligonychus punicicus), acanthopanax gracilis (Oligonychus planus), acanthopanax gracilis (Oligonychus fasciatus), acanthopanax gra (Oligonychus fasciatus (Orchidonus), acanthopanax gra (Orthostachys gracilius), acanthopanax gracilius (Orthostachys (Orchidonus) and Acarus (Orthostachys spp.), rust mite (Phylloptruta oeivora), dermatetranychus multidigitali, dermatophagoides tarsonnei (Polyphagordonemus latus), dermatophagoides (Psoroptes spp.), rhipicephalus spp, rhizophus spp, root mite spp, sarcoptes spp, scorpion maurus, dermatophagoides spp, stepronia spp, oryza minutissima (Steneotarsonemus spp), tarsonemus spp, for example Tarsonemus contusius, tarsonemus albus, tetranychus pallidus, tetranychus spp, for example Tetranychus canadens, tetranychus cinnabarinus, tetranychus turkis turkestani, tetranychus urticae, tetranychus urticae, trombicula alurgesii, vaejovis spp, tomato dorsal tumor gall mite (Vasates lycopersici);
Pests from the Chilopoda class (Chilopoda), such as Geophilus spp (Geophilus spp.), scutigera spp.;
pests from the class of the phylum Collembola (Collembola), such as the armed springtail (Onychiurus armatus); skipper (smithhurus viridis);
pests from the order of the Diplopoda (Diplopoda), such as the species Chilopoda (Blaniulus guttulatus);
pests from the class Insecta (Insecta), for example the order Blattaria (Blattodea), for example Blatta orientalis (Blatta orientalis), blatta asiatica (Blattalla asahinai), blatta germanica (Blattalla germanica), blattella maderae (Leucophaea maderae), loboptera decipiens, house Blatta cockroaches (Neostylopyra rhombifolia), copaia (Panchlora spp.), eupolyphaga (parkablata spp.), periplaneta (percolatea spp.), periplaneta (Periplaneta spp.), e.g. american cockroach (Periplaneta americana), australian cockroach (Periplaneta australiana), periwinia burania (pyrocnoschella surrinamansis), palmaria palmifolia (superella longipapa);
pests from the order Coleoptera (Coleoptera), for example Acalymma vitetum, phaseolus vulgaris (Acanthoscelides obtectus), rhynchophorus rhynchophylla (Adoretus spp.), acethonium cellularis (Aethina tuba), rhagophthalmus populi (Agrastica albi), agrilus spp., for example, agrilus planipennis, agrilus coxalis, agrilus bifilaris, agrilus anxius, straus scholaris (Agriotes p.), such as, for example, agriotes linneatus, flammulina tritici (Agriotes manicus), blackia (Alphiobius diaperinus), poecia tuberosa (Amphiamaron solstitialis), thielavia furcifera (Anobium punctatum), asterina (Anoplophora spp.), such as, for example, anopilus glabra (Anoplophora globiformis), anodon spp., such as, for example, ardisia gossypii (Anthonomus grandis), bark beetle (Anthragmas spp.), the genus Rhynchophorus (Apion sp.), the genus Arundinaria (Apogonia sp.), the genus Cryptonya (Atomaria sp.), such as beet Cryptonya purpurea (Atomaria linearis), pissodes piscicola (Attagenus sp.), baris caulescens, pediophorus medicinalis (Bruchidus obtusifolia), pissodes piscicola (Brucheus sp.), such as pisiform pisum piscicola (Bruchus pisorum), pissodes piscus piscicola (Cassida sp.), california purpurea (Ceratophylla trifoliata), ceratophylla purpurea (Cerotophylla trifoliata), pieris turcica (Ceratophycus sp.), such as Ceratophycus pisum, ceratophycus andrenes, ceratophys androides, brassica lepta, brassica purpurea, brassica lepta purpurea (Charcot) and Pleurotus purpurea species, such as Cooperita, pleurotus purpurea, pleurotus spp. Such as banana weevils (Cosmolides sordidus), sinkian costellobia (Costelytra zealandica), ctencea spp, and weevils (Curculio spp), such as walnut weevils (Curculio carya), curculio caryophyllus, curculio obtusifolia, curculio sayi, trimerella ruscus (Cryptothecium ferrugineus), trimerella lineata (Cryptothecium Pusillus), populus cantoniensis (Cryptorhus lapathii), cryptotheca japonica, dithiopica (Cryptothecoides), dithiopica (Cylindrocarpus spp), dendrophyllus spp, and Dendrophyllus spp (Descurus spp), such as Dendrophyllus spp, and Dendrophyllus spp (Dendrophyllotus spp), such as Cylindrocarpus spp, dithiopica spp, and Dendrodendron beetles spp (Dendrobius spp), such as Juglans spp, and Dendrophyllus spp (Dendrobius spp), such as Diabrotica cucullata (Diabrotica bata), northern corn rootworm (Diabrotica barberi), diabrotica oleracea (Diabrotica undinacea Howardata Howardii), diabrotica undinaceae, diabrotica undivided and Candida domestica (Diabrotica virgifera), corn rootworm (Diabrotica virgifera zeae), diabrotica cantonensis (Diabrotica virgifera), diabrotica spp (Dichlorocis chinensis spp.), rice Diabrotica griffonia armigera (Dicladica), dialloderma spp., epideus spp., food-feeding calabas spp (Epiljuna spp.), such as Cucurbita maxima (Epilacca boreale), mexican bean worm (Pieris variella spp.), epilaria spicata spp (Epilaria juba), phytocida (Epsilox), phytocida spp. (Puccinia purpurea), phytocida (Epsilox, fabricius (Puccinia spp.), or Purpura spp.), cabbage borer (Hellula undaria), black-foot beetle (Heterophycus artemisiifolia), holotrichia diomphalia sp.sp.genus, hylamorpha elegans, north American beetle (Hypertrupes bajulus), california gracilis (Hypera pottica), blue-green elephant (Hypermes squarosus), mipochromus sp.sp.Mippon (Hyperthenemus sp.sp.sp.), such as Coffea arabis (Hyperphynemus happhycus), scopus minor (Hyperthece obstrus), hypothecus pubescens (Hyperthece pubescens), calomelas (Hyperthece moslus sp.sp.mosa), spathodes palmaria moseriana (Lachophyceae), sporophycus pallidus, spathodes (Lamiopsis luteorhyalophycus), sporophys luteorhigera (Melothria, sphacis), sphacea sinensis (Melothrix), sphacea (Melothrix), sphacelaeophycus, sphacea tetranychus (Melothrix), sphacea (Melothria, melothria spp), melothria spp.sp.sp.e (Melothria, melothria spp), melothria spp.sp.sp.sp.sp.sp.sp.sp., oryzaphagus oryzae, genus Elephora (Ocorhynchus spp.), such as Achilles albus (Ocorhynchus crispalis), medicago sativa (Ocorhynchus angusticus), medicago sativa (Ocorhynchus angustictus), medicago sativa (Ocorhynchus ovatus), anacardia robustus (Ocorhynchus), anacardia nigra (Ocorhycus), acropora terrestris (Ocorhynchus), such as Aconitum nigra (Ocimum melanopus), anacardia oryzae (Ocorhynchus oryzae), anacardia miniata (Ocycnopsis benthamus), anacardia septemporalis (Ocychia eutropa), anacardia similis (Pharmacopeia cochinus), anacardia palustra (Phyllotreta), phyllophaga (Phyllotreta), and Phyllotreta (Phyllotreta), such as Phrythrix striatum, and Morifolium striatum (Phyllota), japanese Stephania japonica (Popilia japonica), andes potatous (Premtrypes spp.), rhynchosia maxima (Prostephanus truncatus), phillips spp (Psyliodies spp.), for example, the genus Solanum flea (Psyliodies affinis), phillips brasiliensis (Psyliodies chrysospora brassica), phillips neglecta (Psyliodies puncata), the genus Aranea (Ptinus spp.), coccinella (Rhizobius ventralis), rhynchophorus (Rhizophora dominica), rhynchophorus spp., rhynchophorus ferrugineus (Rhynchophorus ferrugineus), rhynchophorus palmatus (Rhynchophorus palmatus), rhynchophorus spp., e.g., scolyphorus ulmoides (Scolyphorus spp.), rhynchophorus spinosus (Sinoxylon Perforans), cereal genus (Sitophilus spp.), such as wheat weevil (Sitophilus grandis), sitophilus lineris, rice weevil (Sitophilus oryzae), maize weevil (Sitophilus zeamais), cryptorhinus acutus (Sphenophorus spp.), medicinal material A (Stegobbium panicum), stem weevil (Sternechus spp.), such as stem weevil (Sternechus paludatatus), symphylales spp., cilium (Tanyymenus spp.), such as corn weevil (Tanychus diolus), indian fiber weevil (Tanychus indica), red bean ash weevil (Tanyymenus pallidus), yellow rice flour beetle (Tenebrio), large bark beetle (Tenebrious spp.), such as Tritoxoplasma (Tripterocarpus spp.), red bean beetle (Trigonolobus), red beetle (Trigonococcus (Trigonolobus), red beetle (Trigonolobus), such as Trigonococcus spp.);
Pests from the order Dermaptera (Dermaptera), such as coastal fertilizer wigs (ansolabis maritime), european bulbous-in-law (Forficula auricularia), red earwigs (Labidura riparia);
pests from the order Diptera (Diptera), such as Aedes spp (Aedes spp.), such as Aedes aegypti (Aedes aegypti), aedes albopictus (Aedes albopictus), aedes tinctorius (Aedes stiticus), aedes fasciatus (Aedes vexans), insecta fascicularis (Agromomyza spp.), such as Dioscorea sativa (Agromoza frondosa), agromobacter parvicoides (Agromomyza parthenophila, dioschus spp. (Anasttrepha spp.), anopheles spp (Anathes spp.), such as Anopheles quadrimaculatus (Anopheles quadratus), anopheles gambiae (Anopheles gambiae), orychus spp (Aspoyyli spp.), fruit fly spp (Bacteroides spp.), such as melon fruit fly (Bacterora), fruit fly trichlora guttifera (Biturera), fruit fly (Bacteroides spp.), fruit fly oil fly (Bacteroides spp.), red-headed blowfly (Calliphora erythrephala), red-headed blowfly (Calliphora vicina), mediterranean fly (Ceratitis capitata), chironomus (Chironomus spp.), chrysomyia (Chrysomya spp.), myrtus (Chrysopsis spp.), tabanus (Chrysomyla pluvialis), cochlomya spp., kangyia (Contarinia spp.), such as the grape gall midge (Contarinia johnsonii), cabbage gall midge (Contarinia natantii), pear leaf gall midge (Contarinia pyrivora), contarinia schulzi, sorghum gall midge (Contarinia sorghicola), flatworm (Contarinia tritici), dermatophagoides pteronyssinus (Cordylobia anthrophaga), midge (cricotrophus sylvestris), culex spp, such as Culex pipiens (Culex pipiens), culex fatigues (Culex quinquefasciatus), culicoides spp, sclerotia spp, cucumis sativus (Dacus oleae), gephysalis spp, such as Gephycidae brassicae, geophilus spp, such as Allium fistulosum (Delia antiaqua), meloidogous rice (Delia coarctata), tartarian rice (Delia florilega), ashland rice (Delia platura), cabbage (Delia radicum), skin flies (Dermatobia hominis), drosophila (Drosophila spp.), such as Drosophila pelveticus (Drosophila melanogaster), drosophila cherry (Drosophila suzukii), rhagophthalmus (Echinocnemus spp.), euleia heraclei, drosophila (Fannia spp.), megasphaera (Gasterophilus spp.), drosophila (Glossina spp.), tabanus (Haematopota spp.), hymenoptera (Hydrellia spp.), drosophila trichotoma (Hydrella spp.), meristella macrocephalus (Hydrella griseola), dirista (Hylemya spp.), phragmitis (Hippoboca spp.), piscas (Hypoderma spp.), muscas (Liriomyza spp.), such as Liriomyza sativae (Liriomyza brassicae), liriomyza sativae (Liriomyza huidobrensis), liriomyza sativae (Liriomyza sativae), lucilia (Lucilia spp.), such as Lucilia cuprina (Lucilia cuprina), lucilia (Lutzomya spp.), mangania (Mansonia spp.), musca (Musca spp.), such as Musca domestica (Musca domestica), serpentis (Musca domestica vicina), musca (Oestrus spp.), swedish wheat straw fly (Oscinella frag), paratanylar spp., paranauterbergiella subbcicta, spodoptera (Pegomya or Pegomyia spp.), such as beet fly (Pegomya beta), beet leaf miner (Pegomya hyoscyami), rubus sudatus (Pegomya hyoscyami), rubus parvus (Pegomya rubivora), chrysomya (Phylloma spp.), physalis (Phytobroma spp.), pisca fly (Piophila casei), asparagus lucida (Phyllophaga spo.), prodipliosis p, daucus carota (Psilola, rous spp.), rous (Rhagopsis spp.), such as cherry fruit flies (Rhagoletis cingulata), walnut fruit fly (Rhagoletis completa), black cherry fruit flies (Rhagoletis faucitis, european sweet cherry fruit fly (Rhagoletis indunferens), blueberry fruit fly (Rhagoletis menda), apple fruit flies (Rhagoletis pomonella), sarcophaga (Sarcophaga spp.), gnat genera (Simulium spp.), such as southern gnat (Simulium meridionale), drosophila (Stomoxys spp.), tabanus (Tabanus spp.), root fly spp (Tetanops spp.), and Daphus spp. (Tipula spp.), such as European Daphus mosquitos (Tipula paludosa), murphus mossamara (Tipusilurus spp.), murashiza sativa (Tipusilurus fasciata), murashiza sativa (Tipula fasciola virgata), papaya fruit fly (Torula typha);
Pests from the order Hemiptera (Hemiptera), such as acitzia acaciaebileyanae, acitzia dodonaeae, psyllids (acitzia monocathoides), locusta capitis (acitida), elongates (Achythiospon spp.), such as Pisum pisum (Achythiophyn pisum), acrogonia spp., aenolamomia spp., petasites (Agonosporina spp.), phthirius spp., (Aleurocithus spp.), whitefly brassicae oleracea (Aleyrodes proteella), whitefly Saccharum sinensis (Aleurolobus barodensis), whitefly lugens (aleurothrix florosus), allocarpara malayensis, and Cerrena spp (Amrasca spp.), such as Amrasca biguella, leafhopper (Amrasca deactans), aphis fabarum (Anuraphila cardui), sclerotia destructor (Amrasia spp.), such as Cerrena spp.; red kidney pellegelia (Aonidiella aurantii), yellow hoof pellegelia (Aonidiella citrina), red coccid (Aonidiella inornata), pymetrozine (aphanomyza piricola piri), aphid (Aphis spp.), for example Aphis citricola (Aphis citricola), aphis fabri (Aphis craccivora), aphis sphaerica (Aphis fabae), aphis strawberrii (Aphis forbesi), aphis glycines (Aphis glysines), aphis gossypii (Aphis gossypii), aphis hederae, aphis illinoisensis, aphis midlotoni, aphis rhamnosus (Aphis nastilii), aphis oleander (Aphis nerii), aphis applianus (Aphis pomi), aphis virginiana (Aphis spiegella), aphis virginiana (Aphis spiaecola), aphis virginopilla, botryama vinifera (Arboridia apices), arytainilla spp, aspela spp, aspidiella spp. Such as Tocophytrium ivoriganum (Aspidiotus nerii), atanus spp, african-channel reticulum aphid (Aulacorhum solani), bemisia tabaci (Bemis tabaci), australian wood louse (Blastopisylla occidentalis), boriogyolaspis melaleuucae, leptosphaeria punctata (Brachycauliflorus heliospora), microphyria microtuberans (Brachybotrys spp.), cabbage aphid (Brevicula brasiliensis), caryophyllus spp (Cacophyllus spp.), such as Leptosphaera pyricularia (Cacophylla pyricularia), oryza nilotica (Calligonia rugosa), capulilinia spp, flagelliforma (Carneotheca lutea), phyllophthora lanuginosa (Ceylophila lanuginosa), phyllophora canella viridans (Ceratophyceae), phyllophora lanuginosa viridans (Ceyloides), phyllophora indica, frankia indica (Ceylophila viridans), frankia indica (Ceylophila viridans (Ceylophila), frankliniella viride (Frankliniella viride) and Frankliniella viride (Frankinii), metarhizium formosanum (Chondraris rosea), aphis juglandis (Chromaphus bru. Juglandica), tolyphaea montana (Chromophaulus aonidum), tolyphaera melanogaster (Chromophaulus arcus), corn leafhopper (Cicadulina mbilla), coccomytus hatila, lecanicillium (Coccus spp.), for example, tolyphaera fusca (Coccus heperidum), eleuphaera ovalis (Coccus longus), ceripophila citri (Coccus rubellum), ceripophila citri (Coccus pseudococca), coccus viridis (Coccus viridis), cryptomyzurus viridis (Cryptomys zuri), cryptonosus spp., phytopus (Cryptomys zurus zuri), cryptonospora spp. Grass coccinella (Drosicha spp.), neurospora spp (Dysapheis spp.), such as Dysapheis apiifolia, plantago major (Dysapheis plantaginea), neurospora lilacina (Dysapheis tulipae), gecko major (Dysmicoccus spp.), empoasca spp (Empoasca spp.), western potato leafhopper (Empoasca abrupucita), potato leafhopper (Empoasca fabae), apple leafhopper (Empoasca maligna), empoasca solana, empoasca stevensi, miyazua (Eriosoma spp.), for example Eriosoma aeropyrum, woolly apple aphid (Eriosoma lanigerum), eriosoma pyricola, cicada (erythoneneura spp.), eucalyptolyma spp, phlebopus (Euphyllura spp.), euscelis bilobatus, lecania (Ferrisia spp.), mesogatella sp (Fiorinia spp.), furcaspis occidentalis, coffea coffea (Geoccocus affeae), glycaspis spp, albizia julibrissin (Heteropsula cubana), heteropsula spinosa, gloryleaf hoppers (Homalodiella coaggata), cerrena persicae (Hyalopterus ardisianus), myzus persicae (Hyalopterus pruni), erysipelothrix sp (Icerya spot), such as Blastus peltatus (Icerya purchasi), pectinopsis peltatus (Ioocerus sp.), pectinatus peltatus (Idiosphaeus), pectinopsis peltatus (Idiosphaeus), laodelphax striatus (Laodelphax striatus), leium spp., such as Leium cotinum coides (= Pink &, paracoccus fasciatus (Paracoccus fasciatus), leysporium olepisum (Leysporium spp), such as Leysporium peltate (Leysporium spp), leysporidium solanum peltatum (Leysporium spp), leysporidium solanum spica (Leysporium sp.), the genus Elephora (Macrosiphum spp.), for example, orthosiphon solani (Macrosiphum euphoides), macrosiphum liii, orthosiphon aristatus (Macrosiphum rosae), aster nodosa (Macrosteles facieferones), mahanarva spp., kaoliang aphid (Melanaaphis sacchara), metaplexis spp., metaplexis prunosa, metaplexis prainus, metaplexis dirhodoroides (Methylophilum dirhodium), phyllophora nigra (Monilia costalis), monobiolis canopis, onychianus spp., such as Phyllophora fistulosa (Myzus aslonicus), phyllophora pruinosa (Myxophys spp.), myxophys persicae (Myxophys persicae), myxophys angularis, myxophys persicae (Myxophys spp.), myxophys nilotis (Myxophys spp.), neurophys nilotis (Neurophys spp.), neurophys nilotis spp.), such as Nephotettix cincticeps, nephotettix nigropicus, nephotettix nigropis, netgigoniella spp, nilaparvata lugens, oncomenopia spp, orthezia praeloga, oryza sativa (Oxya chinensis), pachypsylla spp, psidium guajava (Parabenaria myrricae), parametriza spp, such as Parametriza cockelli, lepidogramma spp, the genus Aphis virens (Pemphigus spp.), such as Aphis virens (Pemphigus bursterius), pemphigus populivenae, cercosphaera zeae (Peregrinus maidis), phlebopus planus (Perkiniella spp.), the genus Lecanis (Phenococcus spp.), such as Phrosthornia lugens (Phenococcus madeiensis), aphis planopilaris (Phenococcus madeiensis), aphis planus (Pheromovis paserinii), aphis verrucosus (Phonodon humuli), rhizopus vitis (Phylloxara spp.), such as Phylloxera devastatrix, phylostoma notatum (Phylloxera nodobilis), pseudobulbus cupreuteri (Pinnaspis aspetrae), verticillium sp, such as Chinemys citriodora (Planococcus citri), prosopidophylla flava, lepidogra piricola (Protopulinaria pyriformis), musca alba (Pseudolacaspis pendaria), lepidula sp (Pseudococcus spp.), such as Lecanicillium citrinum (Pseudococcus calcoelaiae), lecanicillium consonii (Pseudococcus comstocki), lecanicillium longicaudatis (Pseudococcus longispinus), lecanicillium vitis (Pseudococcus maritimus), lecanicillium dulcamara (Pseudococcus virurni), psyllium (Psylococcus spp.), psyllium (Psyllium spp.), pyriella spp, chimaphila spp, such as juglans regiae (Quadrapidious spp), chimaphila populi (Quadrapidious magna), chimaphila populi (Quadrapidious ostreatus), tocopaipualis (Quadrapidious ostreatus), piropteriopsis pyrifera (Quadrapidious perniciosus), quesada gigas, triplostegia pustus (Rastrococcus spp.), pimpinella spp, such as corn aphid (Rhopalosiphum maidis), apple aphid (Rhopalosiphum Oxyacanthae), corn aphid (Rhopalosiphum padi), red-belly aphid (Rhopalosiphum rufiab), black-armyworm (Saissetia spp.), such as black armyworm (saisselia coffiee), saisselia miranda, saisselia neglecta, olive black armyworm (saisselia oleae), grape leafhopper (scaphoides titanium), schizaphis graminis (Schizaphis graminum), scutellariae (selenious articularis), sipunculus pseudochinensis, sipha flava, sitobion avenae (Sitobion aveae), liptera faberi (Sogata spp.), white-backed planthopper (Sogatella furcifera), aeolian rice (sogato spp.), sticotocephala felina, tree powder louse (siponiensis), tenata malayanensis, tetranectophelea spp, american walnut aphid (tuchayomyces persicae), and the like, such as, for example, binary orange aphids (Toxoptera aurantii), orange aphids (Toxoptera citricidus), greenhouse whitefly (Trialeurodes vaporariorum), pepper louse (Trioza spp.), such as the plant louse persimmon (Trioza diospyri), the genus lesser leafhopper (typlocyba spp.), the genus mesochitum (Unaspis spp.), the genus botrytis viticola (Viteus vitifolii), the genus bombyx (Zygina spp.);
Pests from the order Heteroptera (Heteroptera), such as Trigonopsis spp (Aelia spp.), ormostorius tinctorius (Anasa tristis), triplopsis versicolor (Antystis spp.), boisea spp, orchidaceae spp (Blissus spp.), triplopsis spp (Caloris spp.), campylomma livida, triplopsis heterophyllus (Cavelerius spp.), cimemix spp (Cimemix spx spp.), cimemix armyworm (Cimex hemipterus), dermata (Cimix bug), dermata stinalis (Cimix bug), dermata (Cimix bug), neuropterus bugs (C. Pellucorum), eupatorium spp (C. Colorum, eutypical spp.), lygus lucorum (C. Plutus, eupatorium), eupatorium fort, lepidorum spp.), lepidorum spp (Lepidorum spp.), green bugs (Nezara spp.), for example, rice green bugs (Nezara viridula), small long bugs (Nysius spp.), oagula spp., pentamidae, quadruped dorsalis (Piesma quadrata), orius bugs (Piezodou spp.), oridonus spp., for example, piezodourius guilidinii, lygus bugs (Psallius spp.), pseudoacystus persea, red bugs (Rhodnius spp.), orychinus theobromus (Sahlgelella siklonius), scaptriscoris castanea, black bugs (Scotopteroporia spp.), ficus capitata (Stenitis nashi), tibraca spp., trypus triatus, tritoxypus triatus;
Pests from the order Hymenoptera (Hymenoptera), for example of the genus Acromycex spp, the genus Brachypoda (Athalia spp), for example of the species Brachypoda wasp (Athalia rosae), the genus Atlanta (Atta spp), the genus Camphora spissus (Camplotus spp), the genus Vespa longispidae (Dolichovespira spp), the genus Tricholoma (Diprion spp), for example of the species Ardisia palustris (Diprion similis), the genus Petasia (Hoplocpa spp), for example of the species cerasus (Hoplocpa cookei), hoplocpa testudinea, the genus Formica fusca (Lasius spp), argentina ant (linipithomycem) humile), imported miropodes (monariom pharaonis), chaeto (paratrechia spp.), paravisula spp, plagiocephala spp (platioleis spp.), trefoil (srex spp.), such as spruce blue tree bee (srex noctilio), red fire ant (Solenopsis invicta), tapinoma spp, white foot dolomi ant (technomolylmex albipes), tree bee (urocera spp.), wasp (Vespa spp.), such as wasp marginatus (spa crab), small fire ant (wassmania aurotura aurotta), black tree bee (Xeris spp.);
pests from the isopod (Isopoda) order, such as Armadillidium vulgare (Armadillidium vulgare), onychium pectinosum (Oniscus asellus), armadillidium globosum (Porcellio scaber);
Pests from the order Isoptera (Isoptera), such as Reticulitermes flavipes (Reticulitermes), reticulitermes hesperus (Reticulitermes hesperus);
pests from the order Lepidoptera (Lepidoptera), such as the species Cerrena punctifera (Achroia grisella), morganella sanguinea (Acronacta major), trichoplusia (Adoxophyceae spp.), such as Trichoplusia gossypii (Adoxophyceae orana), trichoplusia (Aedia leucotomelas), gecko (Agrimonia spp.), such as the species Gekko huang (Agrotis segem), trichoplusia microglobus (Agrotis ipsilon), trichopsis undulata (Alabama spp.), such as the species Trichopsis gossypii (Alabama argillacea), the species Selaginella (Amylos tetranyensis), the species Trichopsis striata (Anarsis spp.), the species Trichopsis fortis litura (Anarsis spp.), the species Trichoplusia spp., trichopsis lata spodoptera.spodoptera, the species Trichopsis fortis gladiata (Arthrophyma), the species Trichophyta spp.), such as the species Trichophyta punctata (Anabaena, and the species Trichophyta (Arthrosporida spp.), such as the species Spodoptera punctata (Alabaga), apple fruit point moth (Blastodacna atra), poa plectra (Borbo cinnara), cotton leaf miner (Bucculus thyubertii) and pine looper (Bupalus piniarius), moth-eating species (Busseola spp.), leaf roller moth species (Cacoecia spp.), tea leaf roller moth (Caloptilia theivora), tobacco leaf roller moth (Capua reptilina), codling moth (Carpoppy pomonella), peach fruit moth (Carposina niponensis), winter worm moth (Cheimatobia brumata), grass borer (Chilo spp.), e.g. Chilo plejadellus, chilo suppersalis (Chilo suppersalis), apple fruit moth (Choroetia pariana), cabbage moth (Choristoneura spp.), barley grass (Chrysodeeixis chapiters), grape fruit moth (Clysia ambiguella), cabbage worm (Cnaphaloearia spp.), cnaphalocrocis medinalis (Cnaphalocrocis medinalis), cnaphalocrocis spp (Cnephasia spp.), theelioma spp (Conopomorpha spp.), mellophora spp (conotrachius spp.), copitarsia spp, cochlearia spp (Cydia spp.), e.g. pisum sativum (Cydia nigriana), codia pomonella (Cydia pomonella), dalla noctuides (dalia pomonella), diaphania spp (Diaphania spp.), dipura septosoma spp, sugarcane (Diatraea saccharalis), dioryctria spp, e.g. Dioryctria zimmermani, dioryza spp (Everdia spp.), ecphalalis (ostrinia persicae), ecphalalis ostrinia persicae (ostrinia nubilalis), pieris furalis (ostrinia indica), pieris indica (Epinella furalis (Epinella punctifera), pieris indica (ostrinia spp.), the genus Spodoptera (Epinotia spp.), the genus Mallotus pallidum (Epiphyspora postvatttana), the genus Trichoplusia (Erannis spp.), erschoviella musculata, the genus Spodoptera (Etiella spp.), the genus Spodoptera (Eudocima spp.), the genus Trichoplusia (Eulichia spp.), the genus Trichoplusia (Eulia spp.), the genus Ligustrum lucidum seu japonicum (Eupoecilia ambiguella), the genus Xanthomonas (Euproctis spp.), the genus Flabella (Euctinathus chrysospora), the genus Heliothis virescens (Euxoa spp.), the genus Ceramia glauca (Feltia spp.), the genus Paraffinula (Galleria mellyrata), the genus Trichoplusia (Gracilla spp.), the genus Gracilaria spp., gracilaria spp.), the genus Gracilaria spp. <xnotran> (Helicoverpa armigera), (Helicoverpa zea), (Heliothis spp.), (Heliothis virescens), (Hofmannophila pseudospretella), (Homoeosoma spp.), (Homona spp.), (Hyponomeuta padella), (Kakivoria flavofasciata), (Lampides spp.), (Laphygma spp.), (Laspeyresia molesta), (Leucinodes orbonalis), (Leucoptera spp.), (Leucoptera coffeella), (Lithocolletis spp.), (Lithocolletis blancardella), (Lithophane antennata), (Lobesia spp.), (Lobesia botrana), (Loxagrotis albicosta), (Lymantria spp.), (Lymantria dispar), (Lyonetia spp.), (Lyonetia clerkella), (Malacosoma neustria), (Maruca testulalis), (Mamestra brassicae), (Melanitis leda), (Mocis spp.), monopis obviella, (Mythimna separata), nemapogon cloacellus, (Nymphula spp.), oiketicus spp., omphisa spp., (Operophtera spp.), oria spp., (Orthaga spp.), (Ostrinia spp.), </xnotran> For example European corn borer (Ostrinia nubilalis), spodoptera exigua (Panolis flamma), spanish littoralis (Parara spp.), heliothis virescens (Pectinophora spp.), for example Helicoverpa armigera (Pectinophora gossypiella), perileococcus spp., phtheirosoma spp., phorimaea (Phorimaea spp.), for example Potato Tuber moth (Phorimaea operculella), citrus leaf miner (Phyllocnidia citra), philotus subfamily small Philotus (Phyllonoryces spp.), for example Phyllocercosoma subcollis virens (Phyllotheca blanocardella), phyllocercosella crata (Phyllotheca), phyllocercospora crataea, phyllosa (Pieris spp.), for example cabbage powder spp. = (Pieris rapae), phyllotheca litura viridans (Pleurotensia), plutella xylostella Plusia punctatus (Plutella), plutella xylostella (Plutella xylostella, plutella xylostella (Plutella xylostella), podesia spp, for example Podesia syringae, plutella xylostella (Prays spp.), spodoptera (Prodenia spp.), heliothis spp (Prodenia spp.), nicotiana tabacum (Protopace spp.), myxoplasma spp (Pseudostereotypical spp.), for example, myxoplasma agnus stella (Pseudoplusia unijunucta), spodoptera frugiperda (Pseudoplusia includens), diabrotica zeae (Pyrasula nubilalis), spodoptera frugiperda (Rachiminula nu), sesbane Photinus spp, for example Schoenbius bipunctifer, sesamia alba spp, for example Sesamia oryzae (Scorpha innotata), sesamia lutescens (Scotia segetum), heliothis virescens (Sesamia spp), for example Sesamia inferens (Sesamia incens), heliothis virescens (Spragothrix spp), heliothis virescens (Spodoptera spp), such as Spodoptera eradia, spodoptera exigua (Spodoptera exigua), spodoptera frugiperda (Spodoptera frugiperda), spodoptera praefica, gymnastia (Stathmopoda spp.), stenoma spp, spodoptera arachnifolia (stomophoryx subspecivella), phyla (synanthon spp.), athyria andella (teca sollanivora), isocoryza (thaummetopia spp.), noctuita (thersia gemmatatalis), trichoplusia anguillia (tenella globosa), trichoplusia elongata (Trichoplusia xylostella), gloomya bageworm (tenella pella pelliota), trichoplusia bissula (tenella bispongiosa), tortriconella (torx spp.), chlamydia (Trichoplusia), trichoplusia virida (Trichoplusia), trichoplusia terrestris (Trichoplusia terrestris), trichoplusia (Trichoplusia, trichoplusia terrestris (Trichoplusia), trichoplusia (Trichoplusia, trichoplusia maculis);
Pests from the order Orthoptera (Orthoptera) or the order skipper (saltoria), such as crickets domestica (Acheta domesticus), dichlplus spp, mole cricket genera (Gryllotalpa spp), such as mole cricket (Gryllotalpa), sugarcane locust genera (thermolyphus spp), migratory locust genera (Locusta spp), such as Locusta migratoria (Locusta migratoria), black locust genera (Melanoplus spp), such as migratory black locust (melanopus degastator), paratanicus usasurnsis, desert locust (schistospore gregaria);
pests from the order of the louse (Phthiraptera), such as the genera zoophthiridae (Damalinia spp.), the genus Haematophus spp, the genus Phthirius (Linoganophus spp.), the genus Phthirius (Pediculus spp.), the genus Rhizopus viticola (Phylloxera vastatrix), the genus Bemisia (Phthirius spp.), the genus Trichlorophectum (Trichophagectes spp.), the genus Psychoptrus niloticus (Trichopsis spp.);
pests from the order rodentia (psoroptera), such as Lepinotus spp, pediculus (lipopeleis spp);
pests from the order Siphonaptera, for example the genus Ceratophyllus (Ceratophyllus spp.), the genus Ctenocephalides (Ctenocephalides spp.), for example Ctenocephalides canis (Ctenocephalides canis), ctenocephalides felis (Ctenocephalides felis), prulipidioides (Pulex irutanans), periplaneta penetrans (Tunga pendans), haemophilus volvulus (Xenopsylla cheopis);
Pests from the order of the Thysanoptera (Thysanoptera), such as Amanita zeae (Anaphenthhrips obscurus), thrips oryzae (Balothrips biformis), chaetaphs leeweni, stachybotrys vinifera (Drepanththrips reuteri), ennetherms flavens, frankliniella (Frankliniella spp.), such as Frankliniella tabacum (Frankliniella fusca), frankliniella occidentalis (Frankliniella occidentalis), frankliniella orientalis (Frankliniella schulteriella schuleri), frankliniella viridans (Frankliniella tritici), frankliniella vaccijuga, frankliniella viridans (Frankliniella Thrips), frankliniella Thrips virginiana (Frankliniella Thrips, frankliniella viridans), frankliniella Thrips (Frankliniella Thrips spp), frankliniella Thrips frathrips (Frankliniella viridans) Scirridis, frankliniella spp), frankliniella Thrips (Frankliniella viridans (Frankliniella spp), frankliniella spp;
pests from the order chlamydiales (zygenoma) (= thysanoptera (Thysanura)), such as chlamydomonas (ctenolepsilon spp.), chlamydomonas (Lepisma sacchara), helminth (Lepismodes inquirius), locoweed (Thermobia domestica);
Pests from the syncytium (symphylla), such as Scutigerella spp, for example white pine (Scutigerella immaculata);
pests from the phylum Mollusca (Mollusca), such as the class Bivalvia (Bivalvia), such as the genus bevaceae (Dreissena spp.);
and pests from the Gastropoda class (Gastropoda), such as the athyria genus (Arion spp.), such as black slugs (Arion ater rufus), the amphioxea genus (biomhalaria spp.), the paullinia genus (Bulinus spp.), the bismus genus (deracraps), the bismus genus (deraras spp.), such as the slippery field slugs (deraras laeve), the cochlear worm genus (Galba spp.), the Lymnaea spp.), the Oncomelania genus (onemia spp.), the ampullaria genus (pomoea spp.), the amber spp.;
plant pests from the phylum Nematoda (nemata), i.e. plant parasitic nematodes (phytoparastic nematodes), in particular the genus Rhynchophylla (aglenorphinium spp.), such as the wild species Argyroidea (aglenorphinium agricola), the genus Argyroidea (Anguinia spp.), such as the species Triticum tritici (Anguinia tritici), the genus Aphelenchus (Aphelenchus spp.), such as the species Globodera arachidicola (Aphelenchus arachididis), the species Globodera fragrans (Aphelenchus fragaria), such as the species Globodera microphylla (Belnolales spp.), the species Globodera longipes (Belnolales longicauda), the species Globodera nodorhius (Beloloides), the species Globodera nodorhodeloides (Burserrulata), the species Globodera macrocarpus spp.), the species Globodera (Burserrulata), the species Globodera (Bulleta), necrotizing nematodes (Cacopamur spp.), such as, for example, the plague necrotizing nematodes (Cacopamur pestis), cyclotella (Criconemella spp.), such as, for example, the Cyclotella curvata (Criconemella curvata), the Cyclotella scripta (Criconemella onoensis), the Cyclotella decorata (Criconemella ornata), the Crocemonemma ruscus, the Cyclotella gracilis (Criconemella xenoplax) (= Cyclotella heterodera (Mesociconema), the genus Strobilus (Criconeomoemous spp.), such as, for example, the Croctonia turbinata, the Croconidiosedes onoense, the Cricones orbicularis oraum orum, the genus Strongyloides (Dilenchus spp.), such as, the Digonococcus trichoderma gladiatum (Globulum), the genus Strongyloides (Globulinella spp.), such as, the genus Photorhabditis (Globodera), helicoptera species (Helicotylenchus spp.), such as Helicotylenchus bisptera (Helicotylenchus dihydra), heterodera semitropica (Hemicoconoides spp.), heterodera spp (Hemicoliophora spp.), heterodera spp (Heterodera spp.), such as Heterodera avenae (Heterodera avenae), heterodera glycines (Heterodera glycines), heterodera schachaponica (Heterodera schachnathii), heterodera spp (Hirschhiella spp.), nematoda (Hoplopoliovirus spp.), londoria spp.), such as Nematoda longata (Londorius spp.), meloidogyne spp., such as Meloidogyne incognita (Meloidogyne incognita), meloidogyne spp. (Meloidogyne incognita), meloidogyne incognita (Meloidogyne incognita), eschericia (Meloinema sp.), nacoblus (Nacobb sp.), heterodera (Neotrynchus sp.), heterodera (Paraphylium spp.), paralexoides (Paragonorrhus spp.), paralichenidae (Paralewisus spp.), paralichenidae (Paralichenospora spp.), paratrichogramma (Paratrichum spp.), such as Paratrichum minor (Paratrichum minor), spirochaetes (Paraphylum spp.), brevibacterium sp (Prathyribachus spp.), such as Brevibacterium punctatus (Pratula penetrus), pseudorhabdophycus spp., plastrumus spp., plectophycus spp., pleurophycus spp.), populus planus (Paralichen spp.), poecium planus (Paralichen spp.), podosphaeus (Paralichen spp.), podosphaera sp., phyllospora spp.), podosphaera Pentaphyllus citricola (Pentaphyllus spp.), schistostachys chrysis spp., schizoctonia spp.), raddicus spp., raphimurinus (Raphimurinus spp.), such as Raphimurinus spp.), nematoda (Rotylenchus spp.), spiraria (Rotylenchus spp.), strongylis (Rotylenchus spp.), strongyloides (Scutellonema spp.), nematoda (Subanguina spp.), burserra (Trichodoros spp.), such as Bredia gallica (Trichodoros obliquus), burseus rudis (Trichodoros primetivus), bredia (Tylenchus spp.), such as Breynia cochleariae (Tylenchus annuatus), and Strongyloides hemithorns (Tylenchus spp.), such as Tylenchus semipenetrans (Tylenchus semipenetrans), and Endochus (Xiphilus spp.), such as Standard Sword (Xipelinema spp.).
At specific concentrations or application rates, the compounds of formula (I) can also be used, as appropriate, as herbicides, safeners, growth regulators or compositions for improving plant performance, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, virucides (including anti-viroid compositions) or as anti-MLO (mycoplasma-like organisms) and RLO (rickettsial-like organisms). It may also be used as an intermediate or precursor for the synthesis of other active ingredients, as the case may be.
Preparation
The invention also relates to formulations comprising at least one compound of the formula (I) as pesticides and to the use forms prepared therefrom, such as dips, drops and spray liquids. Optionally, the use forms comprise further pesticides and/or adjuvants which improve the action, such as penetrants, for example vegetable oils (e.g. rapeseed oil, sunflower oil), mineral oils (e.g. paraffin oil), alkyl esters of vegetable fatty acids (e.g. rapeseed oil methyl ester or soybean oil methyl ester) or alkanol alkoxylates; and/or spreading agents (spreaders), such as alkyl siloxanes and/or salts, such as organic or inorganic ammonium or phosphonium salts, for example ammonium or diammonium sulphate; and/or retention promoters, such as dioctyl sulfosuccinate or hydroxypropyl guar polymers; and/or humectants, such as glycerol; and/or fertilizers, such as ammonium-, potassium-or phosphorus-containing fertilizers.
Conventional formulations are, for example, water-Soluble Liquors (SL), emulsion Concentrates (EC), aqueous Emulsions (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule Concentrates (CS); these and other possible formulation types are described, for example, by the International Crop Life organization (Crop Life International) and are described in: pesticide Specifications (pesticides), manual on development and use of pesticides and use of FAO and WHO Specifications for pesticides, and United nations food and agriculture organization Plant Production and Protection literature-173 (FAO Plant Production and Protection Papers-173) (made by the United nations food and agriculture organization/world health organization for the Joint conference of Pesticide Specifications, 2004, ISBN 9251048576). The formulations optionally comprise, in addition to one or more compounds of formula (I), further agrochemical active ingredients.
Preference is given to formulations or use forms which comprise: adjuvants, such as extenders, solvents, spontaneous promoters, carriers, emulsifiers, dispersants, antifreeze compositions, biocides, thickeners; and/or other adjuvants, such as adjuvants. In the context of the present invention, an adjuvant is a component that enhances the biological effect of a formulation, without the component itself having any biological effect. Examples of adjuvants are compositions that promote retention, spreading, attachment to the surface of the leaf or penetration.
These formulations are prepared in a known manner, for example by mixing a compound of formula (I) with auxiliaries, for example extenders, solvents and/or solid carriers and/or further auxiliaries, for example surfactants. The formulations are prepared in a suitable facility or before or during application.
The adjuvants used may be substances which are suitable for imparting specific properties (for example certain physical, technical and/or biological properties) to the formulations of the compounds of the formula (I) or to the use forms prepared from these formulations (for example ready-to-use pesticides such as spray liquids or seed dressing products).
Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example selected from aromatic and nonaromatic hydrocarbons (e.g. paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which, if appropriate, may also be substituted, etherified and/or esterified), ketones (e.g. acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (e.g. N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (e.g. dimethyl sulfoxide).
If the extender used is water, it is also possible to use, for example, organic solvents as cosolvents. Useful liquid solvents are mainly: aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or ethylene glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
In principle, all suitable solvents can be used. Examples of suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes; chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride or dichloromethane; aliphatic hydrocarbons such as cyclohexane, paraffin, petroleum fractions, mineral oils and vegetable oils; alcohols, such as methanol, ethanol, isopropanol, butanol or ethylene glycol, and ethers and esters thereof; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; a strongly polar solvent, such as dimethyl sulfoxide, and water.
In principle, all suitable carriers can be used. Suitable carriers more particularly include the following: for example ammonium salts and finely ground natural rocks such as kaolin, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and finely ground synthetic rocks such as highly dispersed silica, alumina, and natural or synthetic silicates, resins, waxes and/or solid fertilizers. Mixtures of such carriers may likewise be used. Useful carriers for granules include: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic powders, and granules of organic materials such as sawdust, paper, coconut shells, maize cobs and tobacco stalks.
Liquefied gaseous extenders or solvents may also be used. Particularly suitable extenders or carriers are those which are gaseous at standard temperature and atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, and also butane, propane, nitrogen and carbon dioxide.
Examples of emulsifiers and/or foaming agents, dispersants or wetting compositions of ionic or nonionic nature or mixtures of these surface-active substances are salts of polyacrylic acids, lignosulfonic acids, phenolsulfonic acids or naphthalenesulfonic acids, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, polycondensates of ethylene oxide with substituted phenols, preferably alkylphenols or arylphenols, salts of sulfosuccinic esters, taurine derivatives, preferably alkyl taurates, phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyhydric alcohols, and derivatives of compounds containing sulfate, sulfonate and phosphate groups, such as alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates, protein hydrolysates, lignosulfite waste liquors and methylcellulose. The presence of a surfactant is advantageous if one of the compounds of formula (I) and/or one of the inert carriers is insoluble in water and if the application is carried out in water.
Further auxiliaries which may be present in the formulations and the use forms obtained therefrom include dyes such as inorganic pigments, for example iron oxide, titanium oxide and prussian blue, and also organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes; and nutrients and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Other components which may be present are stabilizers, for example low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other compositions which improve the chemical and/or physical stability. A foaming agent (foam generator) or defoamer may also be present.
Furthermore, the formulations and the use forms obtained therefrom may also comprise the following as further auxiliaries: stickers (stickers) are, for example, carboxymethylcellulose, and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate, in the form of powders, granules or latices, or natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other adjuvants may be mineral and vegetable oils.
If appropriate, further auxiliaries may also be present in the formulations and the use forms obtained therefrom. Examples of such additives are fragrances, protective colloids, adhesives, thickeners, thixotropic agents, penetrating agents, retention promoters, stabilizers, chelating agents, complexing compositions, humectants, spreading agents. In general, the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
Useful retention promoters include all those that reduce dynamic surface tension, such as dioctyl sulfosuccinate; or all those that increase viscoelasticity, such as hydroxypropyl guar polymer.
In the context of the present invention, penetrants which may be used are all those substances which are generally used to improve the penetration of agrochemical active ingredients into plants. In the context of the present invention, an osmotic agent is defined by: which penetrate into the plant cuticle from the (usually aqueous) application liquid and/or from the spray coating and thus increase the ability of the active ingredient to migrate in the cuticle. This property can be determined using methods described in the literature (Baur et al, 1997, pesticide Science 51, 131-152). Examples include alcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecyl ethoxylate (12); fatty acid esters such as rapeseed oil methyl ester or soybean oil methyl ester; fatty amine alkoxylates such as tallow amine ethoxylate (15); or ammonium and/or phosphonium salts, for example ammonium sulfate or diammonium phosphate.
The formulation preferably comprises from 0.00000001% to 98% by weight of the compound of formula (I), more preferably from 0.01% to 95% by weight of the compound of formula (I), most preferably from 0.5% to 90% by weight of the compound of formula (I), based on the weight of the formulation.
The content of the compounds of the formula (I) in the use forms prepared from the formulations, in particular pesticides, can vary within wide limits. The concentration of the compounds of the formula (I) in the use forms can generally be from 0.00000001 to 95% by weight, preferably from 0.00001 to 1% by weight, of the compound of the formula (I), based on the weight of the use form. Application is carried out in a conventional manner suitable for the form of use.
Mixture of
The compounds of formula (I) may also be used in admixture with one or more suitable of the following: fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbial agents, beneficial organisms, herbicides, fertilizers, bird repellents, phytotoxins (phytonics), antiproliferative agents, safeners, semiochemicals and/or plant growth regulators, for example, to broaden the spectrum of action, to prolong the period of action, to increase the rate of action, to prevent rejection (repellency) or to prevent the development of resistance. Furthermore, such active ingredient combinations may improve plant growth and/or increase tolerance to abiotic factors, for example to high or low temperatures, to drought or to high water content or soil salinity. Also, flowering and fruiting performance can be improved, germination capacity and root development optimized, harvest is promoted and yield is increased, maturation is affected, quality and/or nutritional value of harvested products is increased, shelf life of harvested products is extended, and/or processability of harvested products is improved.
Furthermore, the compounds of formula (I) may be present in a mixture with other active ingredients or semiochemicals such as attractants and/or bird repellents and/or plant activators and/or growth regulators and/or fertilizers. Likewise, the compounds of formula (I) may also be used to improve plant performance, such as growth, yield and quality of harvested material.
In a particular embodiment of the invention, the compounds of the formula (I) are present in the formulations or the use forms prepared from these formulations in the form of mixtures with other compounds, preferably those as described below.
If one of the compounds described below can exist in different tautomeric forms, these forms are also included, even if not explicitly mentioned in each case. If, as the case may be, all of the mixing components mentioned are capable of forming salts with suitable bases or acids on the basis of their functional groups, they may also form salts with suitable bases or acids.
Insecticide/acaricide/nematicide
The active ingredients specified herein by their common names are known and described, for example, in "The Pesticide Manual", 16 th edition, british Crop Protection Council2012, or may be retrieved over The internet (e.g., http:// www. The Classification is based on the IRAC Mode of Action Classification Scheme (IRAC Mode of Action Classification Scheme) applicable at the time of filing the patent application.
(1) Acetylcholinesterase (AChE) inhibitors, such as carbamates, such as bendiocarb (alanycarb), aldicarb (aldicarb), bendiocarb (bendiocarb), benfuracarb (benfuracarb), butocarb (butocarboxim), ketocarb (butoxycarbxim), carbaryl (carbaryl), carbofuran (carbofuran), carbosulfan (carbosulfan), ethiofencarb (ethiofencarb), fenobucarb (fenobucarb), varacetam (formanate), furathiocarb (furathiocarb), isoprocarb (isoprocarb), methiocarb (methiocarb), methomyl (methomyl), metolcarb), oxamyl (oxamyl), pirimicarb (pirimicarb), propoxur (propcur), thiodicarb (thiodicarb), thiacarb (triazocarb), triazocarb (trimethacarb (XMcarb), and trimethacarb (XMcarb), or organic phosphates, such as acephate (acephate), azamethiphos (azamethiphos), acenphos-ethyl, acenphos-methyl, cadusafos (cadusafos), phosphorus oxychloride (chlorethoxyfos), chlorfenvinphos (chlorefenvinphos), chlorthiophos (chlorephos), chlorpyrifos (chlorethifos-methyl), coumaphos (coumaphos), cyanophos (cyanomethyl), demeton-S-methyl), diazinon (diazinon), dichlorvos/DDVP, chlorothalofop (dicrotophos), dimethoate (dimethoate), chlorfenvinphos (dimethyvinphos), disulfoton (disulphon), thiophen (EPN), ethion (ethion), ethoprophos (ethoprophos), famphur (famchur), fenamiphos (fenamiphos), fenitrothion (fenitrothion), fenthion (fenthion), fosthiazate (fosthiazate) heptenophos (heptanophos), imicyfos, isooxyphos (isooxyphos), isopropyl O- (methoxyaminothiophosphoryl) salicylate (isoproyl O- (methoxyiminothiophosphoryl) salicylate), isoxathion (isoxathion), malathion (malathion), methidathion (mecarbam), methamidophos (methamidophos), methidathion (methidathion) Sulfoprophos (mevinphos), monocrotophos (monocrotophos), naled (naled), omethoate (omethoate), sulfoxyphos (oxydemeton-methyl), parathion-methyl (parathion-methyl), phenthoate (phenthoate), phorate (phorate), phosmet (phosmet), phosphamide (phosphamidon), phoxim (phoxim), pirimiphos-methyl (pirimiphos-methyl), profenofos (propenofos), pyrifos (propathos), prothiofos (prothiofos), pyraclofos (pyraclofos), pyridaphenthion (pyripyrophos), quinalphos (quinalphos), sulfotep (sulfotep), butylpyrimidine (tebufumphos), thion (temephos), terbufos (terbufos), chlorfenvinphos (tetrachlorovinphos), fosetyl (thiometon), triazophos (triazophos), trichlorfon (triclorfon), and triazophos (vamidothion).
(2) GABA-gated chloride channel blockers, such as cyclopentadiene organochlorines, e.g. chlordane (chlordane) and endosulfan (endosulfan), or phenylpyrazoles (fiproles), e.g. ethiprole (ethiprole) and fipronil (fipronil).
(3) Sodium channel modulators, such as pyrethroids, such as, for example, bifenthrin (acrinathrin), allethrin (allethrin), d-cis-trans allethrin, d-trans allethrin, bifenthrin (bifenthrin), bioallethrin (bioallethrin), bioallethrin S-cyclopentenyl isomer, bioresmethrin (bioresmethrin), cycloprothrin (cycloprothrin), cyfluthrin (cyfluthrin), beta-cyfluthrin, cyhalothrin (cyhalothrin), lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin (cypermethrin), alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, gamma-cyhalothrin, beta-cypermethrin, theta-cypermethrin cyphenothrin [ (1R) -trans isomer ] (cyphenothrin [ (1R) -trans isomer ]), deltamethrin (deltamethrin), dexenynthrin [ (EZ) - (1R) isomer ] (empenthrin [ (EZ) - (1R) isomer ]), esfenvalerate (esfenvalerate), ethofenprox (etofenprox), fenpropathrin (fenpropathrin), fenvalerate (fenvalenate), flucythrinate (fluythrinate), flumethrin (flumethrin), tau-fluvalinate (tau-fluvalinate), benzyl ether (halfenprox), imiprothrin (imisprothrin), kadethrin (kadethrin), momflutrin, permethrin (permethrin), permethrin [ (1R) -trans isomer ] (phenothrin) isomer), prallethrin, pyrethrins, tetramethrin [ (1R) isomer ] (tetramethrin [ (1R) isomer) ], tralomethrin and transfluthrin, or dichlorodiphenyl trichloroethane (DDT), or methoxydiphenyl trichloroethor.
(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, such as neonicotinoids (neonicotinoids), for example acetamiprid (acetamiprid), clothianidin (clothianidin), dinotefuran (dinotefuran), imidacloprid (imidacloprid), nitenpyram (nitenpyram), thiacloprid (thiacloprid) and thiamethoxam, or nicotine (nicotinine), or sulfoxaflor (fluroxypyr), or fluroxypyr (flupyradifurone).
(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as spinosyns, e.g., spinetoram (spinetoram) and spinosad (spinosad).
(6) Glutamate-gated chloride channel (GluCl) allosteric modulators, such as avermectins (avermectins)/milbemycins (milbemycins), for example, abamectin (abamectin), emamectin benzoate (emamectin benzoate), lepimectin (lepimectin), and milbemectin (milbemectin).
(7) Juvenile hormone mimics, such as juvenile hormone analogs, e.g. methoprene (hydroprene), methoprene (kinoprene) and methoprene (methoprene), or fenoxycarb (fenoxycarb), or pyriproxyfen (pyriproxyfen).
(8) Other non-specific (multi-site) inhibitors, such as alkyl halides, e.g., methyl bromide and other alkyl halides; or chloropicrin (chloropicrin) or sulfuryl fluoride (sulfuryl fluoride) or borax (borax) or tatarine (tatar ethic) or methyl isocyanate generating agents such as dazomet (dazomet) and metam (metam).
(9) Chordal organ (chordinal organ) regulators, for example pymetrozine or flonicamid.
(10) Mite growth inhibitors, such as clofentezine (cloventezine), hexythiazox (hexythiazox) and flutenzine (diflovidazin), or etoxazole (etoxazole).
(11) Insect gut membrane microbial disruptors, for example Bacillus thuringiensis subspecies israelensis, bacillus sphaericus (Bacillus sphaericus), bacillus subtilis subspecies aizawai, bacillus thuringiensis subspecies kurstaki, bacillus thuringiensis subspecies walkers (Bacillus thuringiensis subspecies tourstaki) and B.t plant proteins: cry1Ab, cry1Ac, cry1Fa, cry1A.105, cry2Ab, VIP3A, mCry3A, cry3Ab, cry3Bb, cry34Ab1/35Ab1.
(12) Mitochondrial ATP synthase inhibitors, for example ATP disruptors, such as diafenthiuron (diafenthiuron), or organotin compounds, such as azocyclotin (azocyclotin), cyhexatin (cyclohexadin) and fenbutatin oxide (fenbutin oxide), or propargite (propagite), or tetradifon (tetradifon).
(13) Uncouplers from oxidative phosphorylation by interrupted proton gradients, such as chlorfenapyr (chlorofenapyr), dinitrocresol (DNOC), and flubendiamide (sulfluramid).
(14) Nicotinic acetylcholine receptor channel blockers such as bensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.
(15) Type 0 chitin biosynthesis inhibitors, such as bistrifluron (bistrifluron), chlorfluazuron (chlorofluazuron), difluorourea (diflubenzuron), flucyclourea (flucycloxuron), flufenoxuron (flufenoxuron), hexaflumuron (hexaflumuron), lufenuron (lufenuron), novaluron (novaluron), noviflumron (novaluron), teflubenzuron (teflubenzuron) and triflumuron (triflumuron).
(16) Type 1 chitin biosynthesis inhibitors, such as buprofezin (buprofezin).
(17) Molt disruptors (especially for diptera), such as cyromazine.
(18) Ecdysone receptor agonists, such as chromafenozide (chromafenozide), halofenozide (halofenozide), methoxyfenozide (methoxyfenozide), and tebufenozide (tebufenozide).
(19) Octopamine receptor agonists, such as amitraz.
(20) Mitochondrial complex III electron transport inhibitors, such as hydramethylnon (hydramethylnon) or acequinocyl (acequinocyl) or fluacrypyrim (fluacrypyrim).
(21) Mitochondrial complex I electron transport inhibitors, such as METI acaricides, for example fenazaquin (fenazaquin), fenpyroximate (fenpyroximate), pyriminofen (pyrimidifen), pyridaben (pyridaben), tebufenpyrad (tebufenpyrad) and tolfenpyrad (tolfenpyrd), or rotenone (Derris).
(22) Voltage-dependent sodium channel blockers, such as indoxacarb (indoxacarb) or metaflumizone (metaflumizone).
(23) Acetyl-coenzyme a (CoA) carboxylase inhibitors, such as tetronic and tetramic acid (tetramic acid) derivatives, for example spirodiclofen (spirodiclofen), spiromesifen (spiromesifen) and spirotetramat (spirotetramat).
(24) Mitochondrial complexes IV electron transport inhibitors, for example phosphines, such as aluminum phosphide, calcium phosphide, phosphines and zinc phosphide, or cyanides, calcium cyanide, potassium cyanide and sodium cyanide.
(25) Mitochondrial complex II electron transport inhibitors, such as β -ketonitrile derivatives (beta-keto nitrile derivatives), for example cyenopyrafen (cyenopyrafen) and cyflumetofen (cyflumetofen) and carboxanilides (carboxanilides), for example pyflubiuride.
(28) Ryanodine (ryanodine) receptor modulators, such as diamides, e.g., chlorantraniliprole (chlorantraniliprole), cyantraniliprole (cyantraniliprole), and flubendiamide (flubendiamide),
<xnotran> , (afidopyropen), (afoxolaner), (azadirachtin), benclothiaz, (benzoximate), (bifenazate), (broflanilide), (bromopropylate), (chinomethionat), (chloroprallethrin), (cryolite), (cyclaniliprole), (cycloxaprid), (cyhalodiamide), dicloromezotiaz, (dicofol), ε - (epsilon metofluthrin), epsilon momfluthrin, flometoquin, fluazaindolizine, (fluensulfone), (flufenerim), (flufenoxystrobin), (flufiprole), fluhexafon, (fluopyram), (fluralaner), fluxametamide, (fufenozide), (guadipyr), heptafluthrin, (imidaclothiz), (iprodione), κ - (kappa-bifenthrin), κ - (kappa-tefluthrin), lotilaner, (meperfluthrin), (paichongding), (pyridalyl), pyrifluquinazon, (pyriminostrobin), spirobudiclofen, (tetramethylfluthrin), (tetraniliprole), (tetrachlorantraniliprole), tioxazafen, (thiofluoximate), (triflumezopyrim) (iodomethane); </xnotran> Further preparations based on Bacillus firmus (I-1582, bioNeem, votivo), and the following compounds: 1- { 2-fluoro-4-methyl-5- [ (2, 2-trifluoroethyl) sulfinyl ] phenyl } -3- (trifluoromethyl) -1H-1,2, 4-triazol-5-amine (known from WO 2006/043635) (CAS 885026-50-6), {1'- [ (2E) -3- (4-chlorophenyl) prop-2-en-1-yl ] -5-fluorospiro [ indole-3, 4' -piperidin ] -1 (2H) -yl } (2-chloropyridin-4-yl) methanone (known from WO 2003/106457) (CAS 637360-23-7) 2-chloro-N- [2- {1- [ (2E) -3- (4-chlorophenyl) prop-2-en-1-yl ] piperidin-4-yl } -4- (trifluoromethyl) phenyl ] isonicotinamide (known from WO 2006/003494) (CAS 872999-66-1), 3- (4-chloro-2, 6-dimethylphenyl) -4-hydroxy-8-methoxy-1, 8-diazaspiro [4.5] dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3- (4-chloro-2, 6-dimethylphenyl) -8-methoxy-2-oxo-1, 8-di-N-yl Azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (known from EP 2647626) (CAS-1440516-42-6), 4- (but-2-yn-1-yloxy) -6- (3, 5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO 2004/099160) (CAS 792914-58-0), PF1364 (known from JP 2010/018586) (CAS registry No. 1204776-60-2), N- [ (2E) -1- [ (6-chloropyridin-3-yl) methyl ] pyridin-2 (1H) -ylidene ] -2, 2-trifluoroacetamide (known from WO 2012/029672) (CAS 1363400-41-2) (3E) -3- [1- [ (6-chloro-3-pyridinyl) methyl ] -2-pyridylidene ] -1, 1-trifluoropropan-2-one (known from WO 2013/144213) (CAS 1461743-15-6), N- [3- (benzylcarbamoyl) -4-chlorophenyl ] -1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole-5-carboxamide (known from WO 2010/051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N- [ 4-chloro-2-methyl-6- (methylcarbamoyl) phenyl ] -2- (3-chloro-2-pyridinyl) pyrazole-3-carboxamide (known from CN 103232431) (CAS 1449220-44-3), 4- [5- (3, 5-dichlorophenyl) -4, 5-dihydro-5- (trifluoromethyl) -3-isoxazolyl ] -2-methyl-N- (cis-1-oxo-3-thiacyclobutyl) benzamide, and pharmaceutically acceptable salts thereof 4- [5- (3, 5-dichlorophenyl) -4, 5-dihydro-5- (trifluoromethyl) -3-isoxazolyl ] -2-methyl-N- (trans-1-oxo-3-thiacyclobutyl) benzamide and 4- [ (5S) -5- (3, 5-dichlorophenyl) -4, 5-dihydro-5- (trifluoromethyl) -3-isoxazolyl ] -2-methyl-N- (cis-1-oxo-3-thiacyclobutyl) benzamide (known from WO 2013/050317 A1) (CAS 2628-83-7), N- [ 3-chloro-1- (3-pyridyl) -1H-pyrazol-4-yl ] -N-ethyl-3-oxazolyl [ alpha ], [ (3,3,3-trifluoropropyl) sulfinyl ] propionamide, (+) -N- [ 3-chloro-1- (3-pyridyl) -1H-pyrazol-4-yl ] -N-ethyl-3- [ (3,3,3-trifluoropropyl) sulfinyl ] propionamide and (-) -N- [ 3-chloro-1- (3-pyridyl) -1H-pyrazol-4-yl ] -N-ethyl-3- [ (3,3,3-trifluoropropyl) sulfinyl ] propionamide (known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1) (CAS 1477923-37-7), 5- [ [ (2E) -3-chloro-2-propen-1-yl ] amino ] -1- [2, 6-dichloro-4- (trifluoromethyl) phenyl ] -4- [ (trifluoromethyl) sulfinyl ] -1H-pyrazole-3-carbonitrile (known from CN 101337937A) (CAS 1105672-77-2), 3-bromo-N- [ 4-chloro-2-methyl-6- [ (methylamino) thiomethyl ] phenyl ] -1- (3-chloro-2-pyridinyl) -1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from CN 103109816A) (CAS 1232543-85-9); n- [ 4-chloro-2- [ [ (1, 1-dimethylethyl) amino ] carbonyl ] -6-methylphenyl ] -1- (3-chloro-2-pyridinyl) -3- (fluoromethoxy) -1H-pyrazole-5-carboxamide (known from WO 2012/034403 A1) (CAS 1268277-22-0), N- [2- (5-amino-1, 3, 4-thiadiazol-2-yl) -4-chloro-6-methylphenyl ] -3-bromo-1- (3-chloro-2-pyridinyl) -1H-pyrazole-5-carboxamide (known from WO 2011/085575 A1) (CAS 1233882-22-8), 4- [3- [2, 6-dichloro-4- [ (3, 3-dichloro-2-propen-1-yl) oxy ] phenoxy ] propoxy ] -2-methoxy-6- (trifluoromethyl) pyrimidine (known from CN 101337940A) (CAS 1108184-52-6); (2E) -2- [2- (4-cyanophenyl) -1- [3- (trifluoromethyl) phenyl ] ethylene ] -N- [4- (difluoromethoxy) phenyl ] hydrazinecarboxamide and 2 (Z) -2- [2- (4-cyanophenyl) -1- [3- (trifluoromethyl) phenyl ] ethylene ] -N- [4- (difluoromethoxy) phenyl ] hydrazinecarboxamide (known from CN 101715774A) (CAS 1232543-85-9); 3- (2, 2-dichlorovinyl) -2, 2-dimethyl-4- (1H-benzimidazol-2-yl) phenyl cyclopropanecarboxylate (known from CN 103524422A) (CAS 1542271-46-4); (4 aS) -7-chloro-2, 5-dihydro-2- [ [ (methoxycarbonyl) [4- [ (trifluoromethyl) thio ] phenyl ] amino ] carbonyl ] indeno [1,2-e ] [1,3,4] oxadiazine-4 a (3H) -carboxylic acid methyl ester (known from CN 102391261A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2, 4-di-O-methyl-1- [ N- [4- [1- [4- (1, 2-pentafluoroethoxy) phenyl ] -1H-1,2, 4-triazol-3-yl ] phenyl ] carbamate ] -alpha-L-mannopyranose (known from US 2014/0275503 A1) (CAS 1181213-14-8); 8- (2-Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (CAS 1253850-56-4), (8-trans) -8- (2-cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (CAS 933798-27-7), (8-cis) -8- (2-cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (formed from WO 2007040280 A1, A1) WO 2007040282 A1 (CAS 934001-66-8), N- [ 3-chloro-1- (3-pyridyl) -1H-pyrazol-4-yl ] -N-ethyl-3- [ (3, 3-trifluoropropyl) thio ] propionamide (known from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9) and N- [4- (aminothiomethyl) -2-methyl-6- [ (methylamino) carbonyl ] phenyl ] -3-bromo-1- (3-chloro-2-pyridyl) -1H- Pyrazole-5-carboxamide (known from CN 103265527A) (CAS 1452877-50-7).
Fungicidal agents
The active ingredients indicated herein by their common names are known and described, for example, in "Pesticide Manual" (16 th edition, british Crop Protection Council) or may be available on the internet (for example:http:// www.alanwood.net/pesticides) And (4) retrieving.
As the case may be, all the mixed components mentioned in the categories (1) to (15) may form a salt with a suitable base or acid if they are capable of forming a salt with a suitable base or acid based on their functional groups. All fungicidal mixture components mentioned in classes (1) to (15) may include tautomeric forms, as the case may be.
1) an inhibitor of ergosterol biosynthesis, for example, (1.001) cyproconazole (cyproconazole), (1.002) difenoconazole (difenoconazole), (1.003) epoxiconazole (epoxyconazole), (1.004) fenhexamide (fenhexamide), (1.005) fenpropidin (fenpropidin), (1.006) fenpropimorph (fenpropimorph), (1.007) fenpyrazamide (fenpyrazamine), (1.008) fluquinconazole (fluquinconazole), (1.009) flutriafol (flutriafol), (1.010) imazalil (imazalil), (1.011) imazalil sulfate (imazalil sulfate), (1.012) ipconazole, (1.013) metconazole (metconazole) (1.014) myclobutanil, (1.015) paclobutrazol (paclobutrazol), (1.016) prochloraz (prochloraz), (1.017) propiconazole (propiconazole), (1.018) prothioconazole (prothioconazole), (1.019) pyrisoxazole (pyrisoxazole), (1.020) spiroxamine (spiroxamine), (1.021) tebuconazole (tebuconazole), (1.022) tetraconazole (tebuconazole), (1.023) triadimenol (triadiminol), (1.024) tridemorph (trimorph), (1.025) triticonazole (triticonazole), (1.026) (1R, 2S, 5S) -5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1-one-yl-methyl-1-one-hydroxy-one) (1H-1, 2, 4-triazol-1-ylmethyl) cyclopentanol, (1.027) (1S, 2R, 5R) -5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1, 2, 4-triazol-1-ylmethyl) cyclopentanol, (1.028) (2R) -2- (1-chlorocyclopropyl) -4- [ (1R) -2, 2-dichlorocyclopropyl ] -1- (1H-1, 2, 4-triazol-1-yl) butan-2-ol, (1.029) (2R) -2- (1-chlorocyclopropyl) -4- [ (1S) -2, 2-dichlorocyclopropyl ] -1- (1H-1, 2, 4-triazol-1-yl) butan-2-ol (1.030) (2R) -2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl ] -1- (1H-1, 2, 4-triazol-1-yl) propan-2-ol, (1.031) (2S) -2- (1-chlorocyclopropyl) -4- [ (1R) -2, 2-dichlorocyclopropyl ] -1- (1H-1, 2, 4-triazol-1-yl) butan-2-ol, (1.032) (2S) -2- (1-chlorocyclopropyl) -4- [ (1S) -2, 2-dichlorocyclopropyl ] -1- (1H-1, 2, 4-triazol-1-yl) butan-2-ol, (1.033) (2S) -2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl ] -1- (1H-1, 2, 4-triazol-1-yl) propan-2-ol, (1.034) (R) - [3- (4-chloro-2-fluorophenyl) -5- (2, 4-difluorophenyl) -1, 2-oxazol-4-yl ] (pyridin-3-yl) methanol, (1.035) (S) - [3- (4-chloro-2-fluorophenyl) -5- (2, 4-difluorophenyl) -1, 2-oxazol-4-yl ] (pyridin-3-yl) methanol, (1.036) 1.2- (4-chloro-2, 4-difluorophenyl) -1, 2-oxazol-4-yl ] (pyridin-3-yl) methanol, (1.036) 1.4-methyl- [2, 4-chloro-2-4-chlorophenyl ] -1, 4-methyl ] -1, 4-oxazol-4-yl } methanol, (1.038) 1- ({ (2S, 4S) -2- [ 2-chloro-4- (4-chlorophenoxy) phenyl ] -4-methyl-1, 3-dioxolan-2-yl } methyl) -1H-1,2, 4-triazole, (1.039) 1- { [3- (2-chlorophenyl) -2- (2, 4-difluorophenyl) oxiran-2-yl ] methyl } -1H-1,2, 4-triazol-5-yl thiocyanate, (1.040) 1- { [ rel (2R, 3R) -3- (2-chlorophenyl) -2- (2, 4-difluorophenyl) oxiran-2-yl ] methyl } -1H-1,2, 4-triazol-5-yl thiocyanate (1.041) 1- { [ rel (2R, 3S) -3- (2-chlorophenyl) -2- (2, 4-difluorophenyl) oxiran-2-yl ] methyl } -1H-1,2, 4-triazol-5-yl thiocyanate, (1.042) 2- [ (2R, 4R, 5R) -1- (2, 4-dichlorophenyl) -5-hydroxy-2, 6-trimethylhept-4-yl ] -2, 4-dihydro-3H-1, 2, 4-triazol-3-thione, (1.043) 2- [ (2R, 4R, 5S) -1- (2, 4-dichlorophenyl) -5-hydroxy-2, 6-tris Methylhept-4-yl ] -2, 4-dihydro-3H-1, 2, 4-triazole-3-thione, (1.044) 2- [ (2R, 4S, 5R) -1- (2, 4-dichlorophenyl) -5-hydroxy-2, 6-trimethylhept-4-yl ] -2, 4-dihydro-3H-1, 2, 4-triazole-3-thione, (1.045) 2- [ (2R, 4S, 5S) -1- (2, 4-dichlorophenyl) -5-hydroxy-2, 6-trimethylhept-4-yl ] -2, 4-dihydro-3H-1, 2, 4-triazole-3-thione (1.046) 2- [ (2S, 4R, 5R) -1- (2, 4-dichlorophenyl) -5-hydroxy-2, 6-trimethylhept-4-yl ] -2, 4-dihydro-3H-1, 2, 4-triazole-3-thione, (1.047) 2- [ (2S, 4R, 5S) -1- (2, 4-dichlorophenyl) -5-hydroxy-2, 6-trimethylhept-4-yl ] -2, 4-dihydro-3H-1, 2, 4-triazole-3-thione, (1.048) 2- [ (2S, 4S, 5R) -1- (2, 4-dichlorophenyl) -5-hydroxy-2, 6-trimethylhept-4-yl ] -2, 4-dihydro-3H-1, 2, 4-triazole-3-thione, 2, 4-dihydro-3H-1, 2, 4-triazole-3-thione, (1.049) 2- [ (2S, 4S, 5S) -1- (2, 4-dichlorophenyl) -5-hydroxy-2, 6-trimethylhept-4-yl ] -2, 4-dihydro-3H-1, 2, 4-triazole-3-thione, (1.050) 2- [1- (2, 4-dichlorophenyl) -5-hydroxy-2, 6-trimethylhept-4-yl ] -2, 4-dihydro-3H-1, 2, 4-triazole-3-thione, (1.051) 2- [ 2-chloro-4- (2, 4-dichlorophenoxy) phenyl ] -1- (1H-1, 2, 4-triazol-1-yl) propan-2-ol, (1.052) 2- [ 2-chloro-4- (4-chlorophenoxy) phenyl ] -1- (1H-1, 2, 4-triazol-1-yl) butan-2-ol, (1.053) 2- [4- (4-chlorophenoxy) -2- (1-trifluoromethyl) phenyl ] -1- (1H-1, 2, 4-triazol-1-yl) butan-2-ol, (1, 4- (4-chlorophenoxy) -2- (1H-phenyl ] -1, 4-triazol-1-yl) butan-2-ol, (1.055) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl ] -1- (1H-1, 2, 4-triazol-1-yl) propan-2-ol, (1.056) 2- { [3- (2-chlorophenyl) -2- (2, 4-difluorophenyl) oxiran-2-yl ] methyl } -2, 4-dihydro-3H-1, 2, 4-triazole-3-thione, (1.057) 2- { [ rel (2R, 3R) -3- (2-chlorophenyl) -2- (2, 4-difluorophenyl) oxiran-2-yl ] methyl } -2, 4-dihydro-3H-1, 2, 4-triazole-3-thione (1.058) 2- { [ rel (2R, 3S) -3- (2-chlorophenyl) -2- (2, 4-difluorophenyl) oxiran-2-yl ] methyl } -2, 4-dihydro-3H-1, 2, 4-triazole-3-thione, (1.059) 5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1, 2, 4-triazol-1-ylmethyl) cyclopentanol, (1.060) 5- (allylthio) -1- { [3- (2-chlorophenyl) -2- (2, 4-difluorophenyl) oxiran-e -2-yl ] methyl } -1H-1,2, 4-triazole, (1.061) 5- (allylsulfanyl) -1- { [ rel (2R, 3R) -3- (2-chlorophenyl) -2- (2, 4-difluorophenyl) oxiran-2-yl ] methyl } -1H-1,2, 4-triazole, (1.062) 5- (allylsulfanyl) -1- { [ rel (2R, 3S) -3- (2-chlorophenyl) -2- (2, 4-difluorophenyl) oxiran-2-yl ] methyl } -1H-1,2, 4-triazole, (1.063) N '- (2, 5-dimethyl-4- { [3- (1, 2-tetrafluoroethoxy) phenyl ] sulfanyl } phenyl) -N-ethyl-N-methyliminocarboxamide (1.064) N' - (2, 5-dimethyl-4- { [3- (2, 2-trifluoroethoxy) phenyl ] thio } phenyl) -N-ethyl-N-methyliminocarboxamide, (1.065) N '- (2, 5-dimethyl-4- { [3- (2, 3-tetrafluoropropoxy) phenyl ] thio } phenyl) -N-ethyl-N-methyliminocarboxamide, (1.066) N' - (2, 5-dimethyl-4- { [3- (pentafluoroethoxy) phenyl ] thio } phenyl) -N-ethyl-N-methyliminocarboxamide -N-methyliminocarboxamide, (1.067) N ' - (2, 5-dimethyl-4- {3- [ (1, 2-tetrafluoroethyl) thio ] phenoxy } phenyl) -N-ethyl-N-methyliminocarboxamide, (1.068) N ' - (2, 5-dimethyl-4- {3- [ (2, 2-trifluoroethyl) thio ] phenoxy } phenyl) -N-ethyl-N-methyliminocarboxamide, (1.069) N ' - (2, 5-dimethyl-4- {3- [ (2, 3-tetrafluoropropyl) thio ] phenoxy } phenyl) -N-ethyl-N-methyliminocarboxamide, and salts thereof (1.070) N ' - (2, 5-dimethyl-4- {3- [ (pentafluoroethyl) thio ] phenoxy } phenyl) -N-ethyl-N-methyliminocarboxamide, (1.071) N ' - (2, 5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methyliminocarboxamide, (1.072) N ' - (4- { [3- (difluoromethoxy) phenyl ] thio } -2, 5-dimethylphenyl) -N-ethyl-N-methyliminocarboxamide, (1.073) N ' - (4- {3- [ (difluoromethyl) thio ] phenoxy } -2, 5-dimethylphenyl) - N-Ethyl-N-methyliminocarboxamide, (1.074) N '- [ 5-bromo-6- (2, 3-dihydro-1H-inden-2-yloxy) -2-methylpyridin-3-yl ] -N-ethyl-N-methyliminocarboxamide, (1.075) N' - {4- [ (4, 5-dichloro-1, 3-thiazol-2-yl) oxy ] -2, 5-dimethylphenyl } -N-ethyl-N-methyliminocarboxamide, (1.076) N '- { 5-bromo-6- [ (1R) -1- (3, 5-difluorophenyl) ethoxy ] -2-methylpyridin-3-yl } -N-ethyl-N-methyliminocarboxamide, (1.077) N' - { 5-bromo-6- [ (1S) -1- (3, 5-difluorophenyl) ethoxy ] -2-methylpyridin-3-yl } -N-ethyl-N-methyliminocarboxamide, (1.078) N '- { 5-bromo-6- [ (1S) -1- (3, 5-difluorophenyl) ethoxy ] -2-methylpyridin-3-yl } -N-ethyl-N-methyliminocarboxamide, (1.074) cis- [ (4-bromo-isopropyl) cyclohexyl) ethoxy ] -2-methylpyridin-3-yl } -N-ethyl-methyliminocarboxamide, (1.077) N' - { 5-bromo-6-isopropyl) cyclohexyl-methyl-propylamide Cyclohexyl) oxy ] -2-methylpyridin-3-yl } -N-ethyl-N-methyliminocarboxamide, (1.080) N' - { 5-bromo-6- [1- (3, 5-difluorophenyl) ethoxy ] -2-methylpyridin-3-yl } -N-ethyl-N-methyliminocarboxamide, (1.081) chlorofluoromethoxy-azole (mefenthiflucarbazole), (1.082) ipfenthiflucarbazole.
2) An inhibitor of the respiratory chain complex I or II, for example, (2.001) benzovindiflupyr (benzovindiflux), (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram (fluopyram), (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr, (2.009) iprothioxanil (isoflutam), (2.010) naphtalidomide (isopyrazam) (trans epimeric enantiomer 1R, SR 4S, 9S), (2.011) naphtalidomide (trans epimeric enantiomer 1S, 012R, 9R), (2.010) naphtalidomide (trans epimeric racemate RS 1RS, SR 4S, 9S) (2.013) Naphthiopyrad (mixture of cis-epimeric racemate 1RS,4SR,9RS and trans-epimeric racemate 1RS,4SR, 9SR), (2.014) Naphthiopyrad (cis-epimeric enantiomers 1R,4S, 9R), (2.015) Naphthiopyrad (cis-epimeric enantiomers 1S,4R, 9S), (2.016) Naphthiopyrad (cis-epimeric racemate 1RS,4SR, 9RS), (2.017) Ames Pentapyram (flufen), (2.018) Thienopyrad (thiopyrad), (2.019) Oxymethylum fluoxapyroxapyroxate (pydeflazafenin), (2.020) pyraziflumizoid, (2.021) Aminoxadine (sedaxane), (2.022) 1, 3-dimethyl-N- (1, 3-trimethyl- 2, 3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.023) 1, 3-dimethyl-N- [ (3R) -1, 3-trimethyl-2, 3-dihydro-1H-inden-4-yl ] -1H-pyrazole-4-carboxamide, (2.024) 1, 3-dimethyl-N- [ (3S) -1, 3-trimethyl-2, 3-dihydro-1H-inden-4-yl ] -1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3- (trifluoromethyl) -N- [2' - (trifluoromethyl) biphenyl-2-yl ] -1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6- (trifluoromethyl) -N- (1, 3-trimethyl-2, 3-dihydro-1H-inden-4-yl) benzamide, (2.027) 3- (difluoromethyl) -1-methyl-N- (1, 3-trimethyl-2, 3-dihydro-1H-inden-4-yl) benzamide, (2.027) 3- (difluoromethyl) -1, 3-methyl-1H-inden- (1, 3-trimethyl-1H-4-indan-4-yl) -benzamide, (2, 028-3-methyl-3-dihydro-1H-1, 3-methyl-3-dihydro-1H-indan-4-yl) benzamide Pyrazole-4-carboxamide, (2.029) 3- (difluoromethyl) -1-methyl-N- [ (3S) -1, 3-trimethyl-2, 3-dihydro-1H-inden-4-yl ] -1H-pyrazole-4-carboxamide, (2.030) 3- (difluoromethyl) -N- (7-fluoro-1, 3-trimethyl-2, 3-dihydro-1H-inden-4-yl) -1-methyl-1H-pyrazole-4-carboxamide, (2.031) 3- (difluoromethyl) -N- [ (3R) -7-fluoro-1, 3-trimethyl-2, 3-dihydro-1H-inden-4-yl ] -1-methyl-1H-pyrazole-4-carboxamide (2.032) 3- (difluoromethyl) -N- [ (3S) -7-fluoro-1, 3-trimethyl-2, 3-dihydro-1H-inden-4-yl ] -1-methyl-1H-pyrazole-4-carboxamide, (2.033) 5, 8-difluoro-N- [2- (2-fluoro-4- { [4- (trifluoromethyl) pyridin-2-yl ] oxy } phenyl) ethyl ] quinazolin-4-amine, (2.034) N- (2-cyclopentyl-5-fluorobenzyl) - N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N- (2-tert-butyl-5-methylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N- (2-tert-butylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N- (5-chloro-2-ethylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) N- (5-chloro-2-isopropylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.039) N- [ (1r, 4s) -9- (dichloromethylene) -1, 3-tetrahydro-1H-pyrazole-4-carboxamide, (2.039) N- [ (1, 3, 4-methyl-1, 4-difluoromethyl) -5-difluoro-methyl-1H-pyrazole-4-carboxamide, (2.040) N- [ (1S, 4R) -9- (dichloromethylene) -1,2,3, 4-tetrahydro-1, 4-methylenenaphthalen-5-yl ] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.041) N- [1- (2, 4-dichlorophenyl) -1-methoxypropan-2-yl ] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.042) N- [ 2-chloro-6- (trifluoromethyl) benzyl ] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N- [ 3-chloro-2-fluoro-6- (trifluoromethyl) benzyl ] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044) N- [ 5-chloro-2- (trifluoromethyl) benzyl ] -N-cyclopropyl-5- (difluoromethyl) -1H-pyrazole-4-carboxamide methyl-N- [ 5-methyl-2- (trifluoromethyl) benzyl ] -1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-fluoro-6-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropyl-5-methylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-thiocarboxamide, (2.049) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.050) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-fluoro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropyl) -1H-pyrazole-4-carboxamide - (2-ethyl-4, 5-dimethylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-fluorobenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-methylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N- (2-cyclopropyl-5-fluorobenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N- (2-cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N- (2-cyclopropylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.
3) An inhibitor of the respiratory chain of complex III, for example, (3.001) ametoctradin (ametoctradin), (3.002) ametryn (amisulbactam), (3.003) azoxystrobin (azoxystrobin), (3.004) toluxastrobin (coumethoxysorbin), (3.005) coumoxystrobin (coumoxystrobin), (3.006) cyazofamid (cyazofamid), (3.007) dimoxystrobin (dimoxystrobin), (3.008) enoximtrobin (enoxabin), (3.009) famoxadone (famoxadon), (3.010) fenamidone (fenamido), (3.011) flufenoxystrobin (flufenoxystrobin), (3.012) fluoxastrobin (fluxastrobin), (3.013) kresoxim (kresoxim-methyl) (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin (pyraclostrobin), (3.018) pyraclostrobin (pyraclostrobin), (3.019) pyraclostrobin (pyraoxystrobin), (3.020) trifloxystrobin (trifloxystrobin), (3.021) (2E) -2- {2- [ ({ [ (1E) -1- (3- { [ (E) -1-fluoro-2-phenylvinyl ] oxy } phenyl) ethylidene ] amino } oxy) methyl ] phenyl } -2- (methoxyimino) -N-methylacetamide, (3.022) (2E, 3Z) -5- { [1- (4-chlorophenyl) -1H-pyrazol-3-yl ] oxy } -2- (methoxyimino) -N, 3-dimethylpent-3-enamide, (3.023) (2R) -2- {2- [ (2, 5-dimethylphenoxy) methyl ] phenyl } -2-methoxy-N-methylacetamide, (3.024) (2S) -2- {2- [ (2, 5-dimethylphenoxy) methyl ] phenyl } -2-methoxy-N-methylacetamide, (3.025) (3S, 6S,7R, 8R) -8-benzyl-3- [ ({ 3- [ (isobutyryloxy) methoxy ] -4-methoxypyridin-2-yl } carbonyl) amino ] -6-methyl-4, 9-dioxo-1, 5-dioxononan-7-yl 2-methylpropionate, (3.026) 2- {2- [ (2, 5-dimethylphenoxy) methyl ] phenyl } -2-methoxy-N-methylacetamide, (3.027) N- (3-ethyl-3, 5-trimethylcyclohexyl) -3-carboxamido-2-hydroxybenzamide, (3.028) (E, 2Z) -5- (1H-chloro-1- { [ 1H-fluoro phenyl) -2-methyl ] acetamide -3-yl ] oxy } -2- (methoxyimino) -N, 3-dimethylpent-3-enamide, methyl (3.029) {5- [3- (2, 4-dimethylphenyl) -1H-pyrazol-1-yl ] -2-methylbenzyl } carbamate.
4) Inhibitors of mitosis and cell division in a subject, for example, (4.001) carbendazim (carbendazim), (4.002) diethofencarb (diethofencarb), (4.003) ethaboxam (ethaboxam), (4.004) fluopicolide (fluopicolide), (4.005) pencycuron (pencycuron), (4.006) thiabendazole (thiabendazole), (4.007) thiophanate-methyl, (4.008) zoxamide (zoxamide), (4.009) 3-chloro-4- (2, 6-difluorophenyl) -6-methyl-5-phenylpyridazine, and (4.010) 3-chloro-5- (4-chlorophenyl) -4- (2, 6-difluorophenyl) -6-methylpyridazine, (4.011) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2, 4, 6-trifluorophenyl) pyridazine, (4.012) 4- (2-bromo-4-fluorophenyl) -N- (2, 6-difluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.013) 4- (2-bromo-4-fluorophenyl) -N- (2-bromo-6-fluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.014) 4- (2-bromo-4-fluorophenyl) -N- (2-bromophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.015) 4- (2-bromo-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.016) 4- (2-bromo-4-fluorophenyl) -N- (2-chlorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.017) 4- (2-bromo-4-fluorophenyl) -N- (2-fluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.018) 4- (2-chloro-4-fluorophenyl) -N- (2, 6-difluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.019) 4- (2-chloro-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.020) 4- (2-chloro-4-chlorophenyl) -1H-pyrazole-5-amine -amine, (4.021) 4- (2-chloro-4-fluorophenyl) -N- (2-fluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.022) 4- (4-chlorophenyl) -5- (2, 6-difluorophenyl) -3, 6-dimethylpyridazine, (4.023) N- (2-bromo-6-fluorophenyl) -4- (2-chloro-4-fluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.024) N- (2-bromophenyl) -4- (2-chloro-4-fluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.025) N- (4-chloro-2, 6-difluorophenyl) -4- (2-chloro-4-fluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine.
5) A compound having multi-site activity capability, for example, (5.001) Bordeaux mixture (Bordeaux mix), (5.002) captafol (captafol), (5.003) captan (captan), (5.004) chlorothalonil (chlorothalonil), (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper sulfate (2 +), (5.010) dithianon (dithianon), (5.011) dodin, (5.012) folpet, (5.013) mancozeb (manzeb), (5.014) maneb), (5.015) metiram, (5.016) metiram, (5.017) hydroxyquinoline copper (copoxline), (5.018) methylneb (metiram), (5.0195.016) metiram and (5.0226) zinc disulfide (5.023) bis (5.023) zinc disulfide (5.023) including (5.023) zinc disulfide, (5.5.5.0226) thiozine and (5.023) zinc disulfide (5.5.5.0226) zinc disulfide (5.023) zinc disulfide: 5,6] [1,4] dithiino [2,3-c ] [1,2] thiazole-3-carbonitrile.
6) Compounds capable of triggering host defenses, such as (6.001) benzothiadiazole (acibenzolar-S-methyl), (6.002) isotianil (isotianil), (6.003) probenazole (probenazole), (6.004) tiadinil (tiadinil).
7) Inhibitors of amino acid and/or protein biosynthesis, for example (7.001) cyprodinil (cyprodinil), (7.002) kasugamycin (kasugamycin), (7.003) kasugamycin hydrochloride hydrate (kasugamycin hydrochloride), (7.004) oxytetracycline (oxytetracycline), (7.005) pyrimethanil, (7.006) 3- (5-fluoro-3, 4-tetramethyl-3, 4-dihydroisoquinolin-1-yl) quinoline.
8) Inhibitors of ATP production, for example (8.001) silthiofam (silthiofam).
9) Cell wall synthesis inhibitors, for example, (9.001) benthiavalicarb (benthiavalicarb), (9.002) dimethomorph (dimethomorph), (9.003) flumorph (flumorph), (9.004) iprovalicarb, (9.005) mandipropamid (manidipamide), (9.006) pyrimorph (pyrimorph), (9.007) propamol (valinate), (9.008) (2E) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one, (9.009) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one.
10 Lipid and membrane synthesis inhibitors, such as (10.001) propamocarb (propamocarb), (10.002) propamocarb hydrochloride (propamocarb hydrochloride), (10.003) tolclofos-methyl.
11 ) melanin biosynthesis inhibitors, for example (11.001) tricyclazole, (11.002) 2, 2-trifluoroethyl { 3-methyl-1- [ (4-methylbenzoyl) amino ] but-2-yl } carbamate.
12 Nucleic acid synthesis inhibitors such as (12.001) benalaxyl (benalaxyl), (12.002) benalaxyl-M) (kiralaxyl), (12.003) metalaxyl (metalaxyl), (12.004) metalaxyl (metalaxyl-M) (mefenoxam).
13 Signal transduction inhibitors such as (13.001) fludioxonil (fluoroxonil), (13.002) iprodione (iprodione), (13.003) procymidone (procymidone), (13.004) proquinazid, (13.005) quinoxyfen (quinoxyfen), (13.006) vinclozolin (vinclozolin).
14 Compounds useful as uncouplers, such as (14.001) fluazinam, (14.002) Dermatophagoides (meptyldinocap).
15 ) other chemical compounds (e.g.) which, for example, (15.001) abscisic acid (abscisic acid), (15.002) thiocyanobenzene (benthiazole), (15.003) bethoxazin, (15.004) carbachomycin (capsomycin), (15.005) carvone (carvone), (15.006) Dermospermam (chinomethionat), (15.007) Thiazol (cufraneb), (15.008) cyflufenamid, (15.009) cymoxanil, (15.010) cyclopropanesulfonamide (cyprosulfamide), (15.011) flutianil, (15.012) fosetyl-aluminium (fosetytyl-alumin), (15.013) calcium fosetytyl-calcium (fosetytyl-calcium), (15.014) sodium fosetsul (sodium) (15.015) methyl isothiocyanate (methyl isothiocyanate), (15.016) metrafenone (metrafenon), (15.017) milomycin (mildiomycin), (15.018) natamycin (natamycin), (15.019) nickel dimethyldithiazole (nickel dimethyldithiocarbamate), (15.020) phthalazine (nitrothaloyl-isoproyl), (15.021) oxamorb, (15.022) fluorothiazolepyrinone (oxathiapiprolin), (15.023) oxifenthiin, (15.024) pentachlorophenol and salts thereof, (15.025) phosphonic acid and salts thereof, (15.026) propamocarb-fosinate (promocarb-fosetyle), (15.027) pyronone (chlazone), (15.028) isobutoquinoline (butoxyquinoline), (15.029) phylloxtalin (tecloftalam), (15.030) methanesulfonamide (tolnifanide), (15.031) 1- (4- {4- [ (5R) -5- (2, 6-difluorophenyl) -4, 5-dihydro-1, 2-oxazol-3-yl ] -1, 3-thiazol-2-yl } piperidin-1-yl) -2- [ 5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl ] ethanone, (15.032) 1- (4- {4- [ (5S) -5- (2, 6-difluorophenyl) -4, 5-dihydro-1, 2-oxazol-3-yl ] -1, 3-thiazol-2-yl } piperidin-1-yl) -2- [ 5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl ] quinazoline, (15.033) 2- (6-benzylpyridin-2-yl) quinazoline, (15.034) 2, 6-dimethyl-1H-1- [ 1H-trifluoromethyl) -1H-pyrazol-1-yl ] propiophenone, (15.033) 2- (6-benzylpyridin-2-yl) quinazoline, (15.034) 2, 6-dimethyl-1H-thia- [ 1H-1-yl ] ethanone (2, 6-di-6-fluoro-1, 6-2-yl ] propiolone (1, 6-fluoro-2-yl) quinazoline-2, 5H-2-propargyl ] ketone -dihydro-1, 2-oxazol-3-yl } -1, 3-thiazol-2-yl) piperidin-1-yl ] ethanone, (15.036) 2- [3, 5-bis (difluoromethyl) -1H-pyrazol-1-yl ] -1- [4- (4- {5- [ 2-chloro-6- (prop-2-yn-1-yloxy) phenyl ] -4, 5-dihydro-1, 2-oxazol-3-yl } -1, 3-thiazol-2-yl) piperidin-1-yl ] ethanone, (15.037) 2- [3, 5-bis (difluoromethyl) -1H-pyrazol-1-yl ] -1- [4- (4- {5- [ 2-fluoro-6- (prop-2-yn-1-yloxy) phenyl ] -4, 5-dihydro-1, 2-oxazol-3-yl } -1, 3-thiazol-2-yl) piperidin-1-yl ] ethanone, (15.038) 2- [6- (3-fluoro-4-methoxy-phenyl) -5-pyridin-1H-yl ] 1- { [ 1H-yl ] ethanone Thiazol-4-yl ] -4, 5-dihydro-1, 2-oxazol-5-yl } -3-chlorophenyl methanesulfonate, (15.040) 2- { (5S) -3- [2- (1- { [3, 5-bis (difluoromethyl) -1H-pyrazol-1-yl ] acetyl } piperidin-4-yl) -1, 3-thiazol-4-yl ] -4, 5-dihydro-1, 2-oxazol-5-yl } -3-chlorophenyl methanesulfonate, (15.041) 2- {2- [ (7, 8-difluoro-2-methylquinolin-3-yl) oxy ] -6-fluorophenyl } propan-2-ol, (15.042) 2- { 2-fluoro-6- [ (8-fluoro-2-methylquinolin-3-yl) oxy ] phenyl } propan-2-ol, (15.043) 2- {3- [2- (1- { [3, 5-bis (difluoromethyl) -1H-pyrazol-1-yl ] acetyl } piperidin-4-yl) -1, 3-thiazol-4-yl ] -1, 3-thiazol-4-yl } -3-chlorophenyl methanesulfonate, (1, 5-dihydro-1H-pyrazol-1-yl) 2-yl ] -1, 3-chlorophenyl methanesulfonate (1, 5-difluoro-5S) -2-yl ] -4-chlorophenyl methanesulfonate Piperidin-4-yl) -1, 3-thiazol-4-yl ] -4, 5-dihydro-1, 2-oxazol-5-yl } phenylmethanesulfonate, (15.045) 2-phenylphenol and its salts, (15.046) 3- (4, 5-trifluoro-3, 3-dimethyl-3, 4-dihydroisoquinolin-1-yl) quinoline, (15.047) 3- (4, 4-difluoro-3, 3-dimethyl-3, 4-dihydroisoquinolin-1-yl) quinoline, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2 (1H) -one), (15.049) 4-oxo-4- [ (2-phenylethyl) amino ] butanoic acid, (15.050) 5-amino-1, 3, 4-thiadiazole-2-thiol, (15.051) 5-chloro-N '-phenyl-N' - (prop-2-yn-1-yl) thiophene 2-sulfonylhydrazide, (15.052) 5-fluoro-2- [ (4-fluorobenzyl) oxy ] pyrimidin-4-amine, (15.053) 5-fluoro-2- [ (4-methylbenzyl) oxy ] pyrimidin-4-amine, and (15.054) 9-fluoro-2, 2-dimethyl-5- (quinolin-3-yl) -2, 3-dihydro-1, 4-benzooxazepine, (15.055) but-3-yn-1-yl {6- [ ({ [ (Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) methylidene ] amino } oxy) methyl ] pyridin-2-yl } carbamate, ethyl (2Z) -3-amino-2-cyano-3-phenylacrylate, (15.057) phenazine-1-carboxylic acid, (15.058) propyl 3,4, 5-trihydroxybenzoate, propyl, (15.059) Quinolin-8-ol, (15.060) Quinolin-8-ol sulfate (2).
Biopesticides as mixed components
The compounds of formula (I) may also be combined with biopesticides.
Biopesticides include, inter alia, bacteria, fungi, yeasts, plant extracts and products formed by microorganisms, including proteins and secondary metabolites.
Biopesticides include bacteria, such as spore-forming bacteria, root-colonizing bacteria, and bacteria that are useful as biopesticides, fungicides, or nematicides.
Examples of such bacteria that are used or that can be used as biopesticides are:
bacillus amyloliquefaciens (Bacillus amyloliquefaciens), strain FZB42 (DSM 231179), or Bacillus cereus (Bacillus cereus), in particular Bacillus cereus strain CNCM I-1562, or Bacillus firmus, strain I-1582 (accession number CNCM I-1582), or Bacillus pumilus (Bacillus pumilus), in particular strain GB34 (accession number ATCC 700814) and strain QST2808 (accession number NRRL B-30087), or Bacillus subtilis (Bacillus subtilis), in particular strain GB03 (accession number ATCC SD-1397), or Bacillus subtilis strain QST713 (accession number NRRL B-21661) or Bacillus subtilis strain OST 30002 (accession number NRRL B-50421), bacillus thuringiensis (Bacillus thuringiensis), in particular of the species Israeli, bacillus thuringiensis israelensis (serotype H-14), strain AM65-52 (accession number ATCC 1276), or Bacillus thuringiensis subsp, AIZAWAI, in particular strain ABTS-1857 (SD-1372), or Bacillus thuringiensis subsp, strain HD-1, or Bacillus thuringiensis subsp, strain NB 176 (SD-5428), bacillus punctatus (Pasteurella penatrans), bacillus pasteurianus (Pasteur), strain Pasteurella sp, strain D-11 (Pasteurella spp.) (Rolenicus strain QRS = R3 (S.succinicschnei) or Streptomyces griseus strain S.sp.) (Streptomyces griseus strain QRS 6134), strain S.aureus (S.aureus) (S.aureus strain S.sp.), NRRL B-50550), streptomyces galbus (Streptomyces galbus) strain AQ6047 (accession number NRRL 30232).
Examples of fungi and yeasts used as or as biopesticides are:
beauveria bassiana (Beauveria bassiana), in particular strain ATCC 74040, chaetomium cupreum (Coniothyrium minitans), in particular strain CON/M/91-8 (accession number DSM-9660), lecanicillium (Lecanicillium spp.), in particular strain HRO LEC 12, verticillium lecanii (Lecanicillium lecanii) (previously known as Verticillium lecanii), in particular strain KV01, metarrhizium anisopliae (Metarrhizium anisopliae), in particular strain F52 (DSM 3884/ATCC 90448), metronicke mei (Metacanicola), in particular strain NRRL Y-30752, paecilomyces fumonis (Paecilomyces fumonis) (now: isaria fumosorosea (Isaria fumosorosea)), in particular strain IFPC 200613 or strain Apopka 97 (accession number ATCC 20874), paecilomyces lilacinus (Paecilomyces lilacinus), in particular Paecilomyces lilacinus strain 251 (AGAL 89/030550), helminthomyces flavus (Talaromyces flavus), in particular strain V117b, trichoderma reesei (Trichoderma atroviride), in particular strain SC1 (accession number CBS 122089), trichoderma harzianum (Trichoderma harzianum), in particular Trichoderma harzianum (T.harzianum rifai) T39 (accession number CNCM I-952).
Examples of viruses used as or as biopesticides are:
examples of such viruses include Spodoptera fusca (Adoxophyalina) (summer fruit leaf roller) Granulosis Virus (GV), codling moth (Cydia pomonella) (codling mood) Granulosis Virus (GV), helicoverpa armigera (cotton bollworm) nucleopolyhedrosis virus (NPV), spodoptera exigua (Spodoptera exigua) (Belgian) mNPV, spodoptera frugiperda (Spodoptera frugiperda) (fall armyworm) mNPV, spodoptera litura (Spodoptera littoralis) (Africa cotton leaf worm (Africa cotton bollworm)) NPV.
Also included are bacteria and fungi which are added to plants or plant parts or plant organs as "inoculants" and which, by virtue of their specific properties, promote plant growth and plant health. Examples include:
agrobacterium (Agrobacterium sp.), rhizobium rhizomae (Azorhizobium caudatum) and Azotobacter (Azotobacter sp.), azotobacter sp.azoniae (Azotobacter sp.), azotobacter sp.azotobacterium (Azotobacter sp.), chronic Rhizobium (Bradyrhizobium sp.), burkholderia (Burkholderia sp.), especially Burkholderia cepacia (Burkholderia cepacia) (formerly known as Pseudomonas cepacia (Pseudomonas cepacia)), burkholderia megaspora (Gigaspora sp.) or Gigaspoora monospora, glomus sp., ceratonia sp.sp., lactobacillus (Lactobacter sp.), lactobacillus sp.lactis (Lactobacter), rhinococcus (Lactobacillus sp.), rhizobium nodosum), rhizobium pararhizobium (Rhizobium sp.), pseudomonas sp., rhizobium (Lactobacillus sp.), pseudomonas sp., rhizobium (Scorzonula), rhizobium (Rhizobium sp.), rhizobium sp.).
Examples of plant extracts and products formed by microorganisms (including proteins and secondary metabolites) used as or as biopesticides are:
garlic (Allium sativum), artemisia absinthium (Artemisia absinthium), azadirachtin (azadirachtin), biokeeper WP, cassia nigricans, celastrus angulatus (Celastrus angulus), chenopodium antalum anthelminticum, chitin, armour-Zen, european Dryopteris filix-mas, equisetum arvense (Equisetum arvense), fortune Aza, fungastop, heads Up (Chenopodium saponin extract (Chenopodium quinoa saponin extract)), pyrethrum (pyrenthrum)/pyrethrin (pyrathrin), sossia amara, quercus (Quercus), quillar (Quaja), quilla, garlia japonica, garva, quasium japonicum, and Quasium nigra TM Insecticides ", rotenone, ryania/ryanodine, comfrey (Symphytum officinale), tanacetum vulgare (Tanacetum vulgare), thymol (thymol), triact 70, triCon, tropieaulum maju, urtica dioica, veratrine (Veratrin), white mistletoe (Thymond), and mixtures thereofExtracts of plants (Brassicaceae), especially rape or mustard flour, from the genus Brassicaceae (Viscum album).
Safeners as mixed components
The compounds of formula (I) may be combined with a safener, examples of such safeners are benoxacor (benoxacor), cloquintocet (-mexyl), chloranil (cyometrinil), cyprosulfamide (cyprosulfamide), dichlormid (dichlormid), fenchlorazole (-ethyl)), fenclorim (fenclorim), fluquinconazole (flurazole), fluxofenim (fluxofenim), fenclozole (furilazole), isoxadifen (-ethyl)), mefenpyr (-diethyl)), naphthalic anhydride (naphthalic anhydride), oxabetrinil (oxabetrinil), 2-methoxy-N- ({ 4- [ (methylcarbamoyl) amino ] phenyl } sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) -1-oxaspiro [ 4.526 ] CAS 3-715, 3-trimethyloxazalane (3-5-trimethyl-3, 5207, 3-dichloro-oxazolidine (CAS) and 523-3-5-trimethyl-oxazalane (trimethacil).
Plants and plant parts
All plants and plant parts can be treated according to the invention. Plants are to be understood as meaning in this context all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye, oats), maize, soya, potatoes, sugar beet, sugar cane, tomatoes, sweet peppers, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leek (leek), beans, cabbage (Brassica oleracea), for example cabbage, and other plant species, cotton, tobacco, rape and fruit plants (the fruits are apples, pears, citrus fruits and grapes). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars protectable or not protectable by the breeders' rights. Plants are understood to mean all developmental stages such as seeds, seedlings, young (immature) plants up to and including mature plants. Plant parts are understood as meaning all parts and organs of plants above and below the ground, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, branches, flowers, fruit bodies, fruits and seeds, and also roots, tubers and rhizomes. Plant parts also include harvested plants or harvested plant parts and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, shoots (slips) and seeds.
The treatment of plants and plant parts with the compounds of the formula (I) according to the invention is carried out directly or by allowing the compounds to act on their environment, habitat or storage space by customary treatment methods, such as dipping, spraying, evaporation, fogging, scattering, painting, injection, and also, in the case of propagation material, in particular in the case of seeds, by applying one or more coatings.
As mentioned above, all plants and parts thereof can be treated according to the invention. In a preferred embodiment, wild plant varieties and plant cultivars or those plants and parts thereof obtained by conventional biological breeding methods such as crossing or protoplast fusion are treated. In a further preferred embodiment, transgenic plants and plant cultivars (genetically modified organisms) and parts thereof which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods, are treated. The term "part" or "part of a plant" or "plant part" has been explained above. According to the invention, it is particularly preferred to treat the plants of the respective commercially available conventional plant cultivars or those in use. Plant cultivars are understood as meaning plants which have novel properties ("traits") and have been obtained by conventional breeding, mutagenesis or recombinant DNA techniques. They may be cultivars, varieties, biotypes or genotypes.
Transgenic plants, seed treatment and integration event
Preferred transgenic plants or plant cultivars (those obtained by genetic engineering) to be treated according to the invention include all plants which, by genetic modification, received genetic material which imparted particularly advantageous, useful properties ("traits") to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity levels, enhanced flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or higher nutritional value of the harvested product, better storage capacity and/or processability of the harvested product. Other and particularly emphasized examples of such properties are: increased resistance of plants to animal pests and microbial pests such as insects, arachnids, nematodes, mites, slugs and snails, and also to phytopathogenic fungi, bacteria and/or viruses caused by, for example, systemic Acquired Resistance (SAR), systemin, phytoalexins, inducers (elicirors) and resistance genes and correspondingly expressed proteins and toxins, and also increased tolerance of plants to certain herbicidally active ingredients such as imidazolinones, sulphonylureas, glyphosate or phosphinothricins (e.g. the "PTA" genes), is caused, for example, by toxins formed in plants, in particular by genetic material from bacillus thuringiensis (e.g. by genes CryIA (a), cryIA (b), cryIA (c), cryIIA (c), cryIIIA, cryIIIB2, cry9c, cry2Ab, cry3Bb and CryIF, and combinations thereof). Genes conferring the desired property ("trait") may also be present in the transgenic plant in combination with each other. Examples of transgenic plants mentioned include important crop plants, such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soybean, potato, sugar beet, sugarcane, tomato, pea and other vegetable varieties, cotton, tobacco, oilseed rape and fruit plants (the fruits are apple, pear, citrus fruits and grapes), with particular emphasis on maize, soybean, wheat, rice, potato, cotton, sugarcane, tobacco and oilseed rape. A particularly emphasized characteristic ("trait") is the increased resistance of plants to insects, arachnids, nematodes and slugs and snails.
Type of crop protection-treatment
The plants and plant parts are treated directly with the compounds of the formula (I) or by acting on their environment, habitat or storage space using conventional treatment methods, such as dipping, spraying, atomizing, irrigating, evaporating, dusting, atomizing, broadcasting, foaming, coating, spreading-on, injection, watering (drenching), drip-irrigation, and for propagation material, in particular for seeds, also by dry seed treatment, liquid seed treatment, slurry treatment, by forming coatings (encrusting), by coating with one or more coatings, etc. The compounds of the formula (I) can also be applied by the ultra-low volume method or the application form or the compounds of the formula (I) can be injected into the soil as such.
The direct treatment of the plants is preferably foliar application, meaning that the compounds of the formula (I) are applied to the leaves, in which case the frequency of treatment and the application rate should be adjusted according to the level of infestation by the pests in question.
For systemic active ingredients, the compounds of the formula (I) can also enter the plant via the root system. The plants are then treated by acting the compounds of formula (I) on the habitat of the plants. This can be done, for example, by: drench, or mix into soil or culture liquid, means to impregnate the locus of the plant (e.g. soil or hydroponic system) with the compound of formula (I) in liquid form; or soil application, meaning that the compounds of formula (I) according to the invention are introduced into the locus of the plants in solid form, for example in the form of granules. For rice crops, this can also be accomplished by metering the compounds of the formula (I) in solid application form, for example in the form of granules, into the flooded rice field.
Seed treatment
The control of animal pests by treating the seeds of plants has long been known and is the subject of constant improvement. However, the treatment of seeds creates a series of problems that are not always solved in a satisfactory manner. It is therefore desirable to develop methods for protecting seeds and germinating plants which do not require or at least significantly reduce additional pesticide application during storage, after sowing or after emergence of the plants. Furthermore, it is desirable to optimize the amount of active ingredient used in order to provide optimum protection of the seeds and the germinating plants from attack by animal pests, while the active ingredient used does not damage the plants themselves. In particular, the methods for seed treatment should also take into account the insecticidal or nematicidal properties inherent to transgenic plants resistant or tolerant to pests, to achieve optimal protection of the seed as well as the germinating plant with a minimum amount of pesticide.
The invention therefore also relates in particular to a method for protecting seeds and germinating plants from attack by pests by treating the seeds with one of the compounds of formula (I). The method of the invention for protecting seeds and germinating plants from attack by pests also comprises a method in which the seeds are treated simultaneously or sequentially in one operation with the compound of formula (I) and the mixed components. It additionally includes methods wherein the seed is treated with the compound of formula (I) and the mixed components at different times.
The invention also relates to the use of compounds of formula (I) for treating seeds to protect the seeds and the resulting plants from attack by animal pests.
The invention also relates to seed which has been treated with a compound of formula (I) according to the invention to protect it from animal pests. The invention also relates to seeds which have been treated simultaneously with a compound of formula (I) and a mixed component. The invention also relates to seeds which have been treated with a compound of formula (I) and a mixed composition at different times. For seeds that have been treated with the compound of formula (I) and the mixed components at different times, the substances may be present in different layers on the seed. In this case, the layers comprising the compound of formula (I) and the mixed components may optionally be separated by an intermediate layer. The invention also relates to such seeds: wherein the compound of formula (I) and the mixed components are applied as part of a coating or as another layer or layers in addition to a coating.
The invention also relates to such seeds: after treatment with the compound of formula (I), it is subjected to a film coating treatment to avoid abrasion of the seeds by dust.
One of the advantages which arises when the compounds of the formula (I) act systemically is that the treatment of the seed protects not only the seed itself but also the plants produced therefrom from attack by animal pests after emergence. In this way, immediate treatment of the crop at or shortly after sowing can be dispensed with.
Another advantage is that treatment of the seed with a compound of formula (I) enhances germination and emergence of the treated seed.
It is also considered advantageous that the compounds of the formula (I) can also be used in particular in transgenic seed.
The compounds of formula (I) may also be used in combination with signal technology compositions to allow better colonization by commensals (e.g. rhizobia, mycorrhiza and/or endophytic bacteria or fungi) and/or to optimize nitrogen fixation.
The compounds of formula (I) are suitable for the protection of seeds of any plant variety used in agriculture, greenhouse, forestry or horticulture. More particularly, the seeds are seeds of cereals (e.g. wheat, barley, rye, millet and oats), maize, cotton, soybean, rice, potato, sunflower, coffee, tobacco, canola (canola), oilseed rape, sugar beet (e.g. sugar beet and fodder beet), peanuts, vegetables (e.g. tomato, cucumber, beans, cruciferous vegetables, onions and lettuce), fruit plants, lawn plants and ornamental plants. Of particular interest are the treatment of the seeds of cereals (e.g. wheat, barley, rye and oats), maize, soya beans, cotton, canola, rape, vegetables and rice.
As mentioned above, it is also of particular importance to treat transgenic seeds with compounds of formula (I). This relates to the seeds of plants which generally contain at least one heterologous gene controlling the expression of a polypeptide having in particular pesticidal and/or nematicidal properties. The heterologous gene in the transgenic seed may be derived from a microorganism such as Bacillus (Bacillus), rhizobium (Rhizobium), pseudomonas (Pseudomonas), serratia (Serratia), trichoderma (Trichoderma), corynebacterium (Clavibacter), gliocladium (Glomus) or Gliocladium (Gliocladium). The present invention is particularly suitable for treating transgenic seed comprising at least one heterologous gene derived from Bacillus. More preferably, the heterologous gene is derived from Bacillus thuringiensis.
In the context of the present invention, the compound of formula (I) is applied to seed. Preferably, the seed is treated in a state where the seed is sufficiently stable to not be damaged during the treatment. In general, the seeds may be treated at any time between harvest and sowing. Seeds that have been isolated from plants and have had the cob, husk, stalk, cuticle, fuzz, or pulp removed are typically used. For example, seeds that have been harvested, cleaned, and dried to a moisture content that allows for storage may be used. Alternatively, seeds which have been dried, treated with, for example, water (e.g., priming), and then dried can also be used. For rice seeds, seeds that have been soaked in, for example, water until they reach a certain stage of the rice embryo ("embryo break stage"), which can stimulate germination and make emergence more uniform, can also be used.
When treating seed, care must generally be taken to select the amount of the compound of formula (I) and/or the amount of the other additives to be applied to the seed so that the germination of the seed is not adversely affected or the resulting plant is not damaged. This must be ensured in particular for active ingredients which can exhibit phytotoxic effects at certain application rates.
Typically, the compound of formula (I) is applied to the seed in a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
The compounds of formula (I) can be converted into conventional seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, pastes or other seed coating compositions, and ULV formulations.
These formulations are prepared in a known manner by mixing the compounds of the formula (I) with the customary additives, such as customary extenders and solvents or diluents, dyes, wetting ingredients (wetting compositions), dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water.
The dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes which are customarily used for such purposes. Pigments that are sparingly soluble in water or dyes that are soluble in water may be used. Examples include dyes known under the names rhodamine B, c.i. pigment red 112, and c.i. solvent red 1.
Useful wetting ingredients which may be present in the seed dressing formulations which can be used according to the invention are all substances which promote wetting and are generally used in the formulation of agrochemical active ingredients. Preferably, alkyl naphthalenesulfonates, such as diisopropyl naphthalenesulfonate or diisobutyl naphthalenesulfonate, can be used.
Suitable dispersants and/or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active ingredients. Preferably, a nonionic or anionic dispersant or a mixture of nonionic or anionic dispersants may be used. Suitable nonionic dispersants include, in particular, ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ether, and also phosphorylated or sulfated derivatives thereof. Suitable anionic dispersants are, in particular, lignosulfonates, polyacrylates and arylsulfonate-formaldehyde condensates.
The antifoams which may be present in the seed dressing formulations which can be used according to the invention are all foam-inhibiting substances which are customary for formulations of agrochemical active ingredients. Silicone antifoaming agents and magnesium stearate can be preferably used.
Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include bischlorophenol and benzyl alcohol hemiformal.
Secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays and finely divided silica.
Useful binders which may be present in the seed dressing formulations which can be used according to the invention are all conventional binders which can be used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and methyl cellulose (tylose).
Gibberellins which may be present in the seed dressing formulations which can be used according to the present invention are preferably gibberellins A1, A3 (= gibberellic acid)A4 and A7; gibberellic acids are particularly preferably used. Gibberellins are known (see R.Wegler "Chemie der Pflanzenschutz-and
Figure GDA0003969167050000921
", vol.2, springer Verlag,1970, pp.401-412).
The seed dressing formulations which can be used according to the invention can be used directly or after prior dilution with water for the treatment of a wide variety of different seed types. For example, the concentrate or the formulation obtainable therefrom by dilution with water can be used for dressing the following seeds: the seeds of cereals (such as wheat, barley, rye, oats and triticale) and of maize, rice, oilseed rape, peas, beans, cotton, sunflowers, soybeans and sugar beets, or of a plurality of different vegetable seeds. The seed dressing preparations which can be used according to the invention or their diluted use forms can also be used for dressing seeds of transgenic plants.
For the treatment of seeds with the seed-dressing formulations which can be used according to the invention or the use forms thereof which are produced by adding water, all mixing units which are generally available for seed dressing are useful. Specifically, the seed dressing process comprises the following steps: the seeds are placed in a mixer in batch or continuous operation, the specifically desired amount of the seed-dressing formulation is added (as such or after prior dilution with water), and mixing is carried out until the formulation is distributed uniformly over the seeds. If appropriate, a drying operation is subsequently carried out.
The application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. Depending on the specific content of the compound of formula (I) in the formulation and the seed. The application rate of the compounds of formula (I) is generally between 0.001 and 50g per kg of seeds, preferably between 0.01 and 15g per kg of seeds.
Animal health
In the field of animal health, i.e. veterinary medicine, the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term "endoparasites" includes in particular helminths and protozoa, such as coccidia (coccidia). Ectoparasites are generally and preferably arthropods, in particular insects or acarids.
In the field of veterinary medicine, the compounds of the formula (I) having advantageous warm-blooded animal toxicity are suitable for controlling parasites which occur in animal keeping and animal rearing of domestic animals, breeding animals, zoo animals, laboratory animals and domestic animals. It is active against all or a specific developmental stage of said parasite.
Agricultural livestock include, for example, mammals, such as sheep, goats, horses, donkeys, camels, buffalos, rabbits, reindeer, deer antlers, and in particular cattle and pigs; or poultry such as turkeys, ducks, geese, and particularly chickens; or fish or crustaceans, for example in aquaculture; or, as the case may be, insects such as bees.
Domestic animals include, for example, mammals, such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and in particular dogs, cats, caged birds; reptiles, amphibians or aquarium fish.
In one embodiment, the compound of formula (I) is administered to a mammal.
In another embodiment, the compounds of formula (I) are administered to birds, i.e. caged birds or in particular poultry.
The use of compounds of formula (I) for the control of animal parasites aims at reducing or preventing diseases, mortality and reduction of performance (for meat, milk, wool, skins, eggs, honey etc.), making animal breeding more economical and simpler and enabling better animal health.
With respect to the field of animal health, in the context of the present invention, the terms "control" or "controlling" mean that a compound of formula (I) is effective in reducing the incidence of a particular parasite in an animal infected with such parasite to a harmless extent. More specifically, "control" means in the context of the present invention that the compounds of formula (I) kill, inhibit the growth or inhibit the reproduction of the respective parasite.
Arthropods include, but are not limited to, for example,
arthropods from the order phthirida (anoplodia), such as the genera diaphorina (haemantoupinus spp.), pediculosis (linogluchus spp.), pediculosis (Pediculus spp.), pediculosis (phthirus spp.), pubic pediculosis (phthirus spp.), and tubostia (solenopots spp.);
arthropods from the order mallophaga (mallophaga) and obtuse (amyycerina) and gracilia (Ischnocerina), such as the genera bovines (Bovicola spp.), pediculus anii (Damalina spp.), and felicis (feliola spp.); lepikentron spp, avicularis (Menopon spp), rodentia (trichoectes spp), trichlous (Trimenopon spp), giant lice (triontopon spp), giant lice (Trinoton spp), werneckiella spp;
arthropods from the Diptera (Diptera) and the subclass Long (Nematocerna) and the subclass short (Brachycerina), such as Aedes (Aedes spp.), anopheles (Anopheles spp.), tabanus (Atylotus spp.), bemisia (Braula spp.), calliptera (Calliphora spp.), chrysomyia (Chrysomyia spp.), tabanus (Chrysospp.), culex (Culex spp.), cuculus (Culicoides spp.), culico (Culicoides spp.). Eugnathus (Eusimulium spp.), latrine (Fannia spp.), gasterophilus (Gasterophilus spp.), glossomyelia (Glossina spp.), ceratitis (Haematobia spp.), flaccid (Haematopota spp.), flaccid (Hippoboca spp.), gadfly (Hybomita spp.), okamackerel (Hybomita spp.), gypennis (Hyvataea spp.). Dermaphyllus (Hypoderma spp.), pediculus ovis (Lipoptena spp.), viridis (Lucilia spp.), phleboptera (lutomyia spp.), tick-fly (mellophagus spp.), moraxella (Morellia spp.), musca (muscla spp.), breviburnus (Odagmia spp.), brachypus (Odagmia spp.), lyssergidus (olestus spp.), philips (philippine), phaeomyia spp.), chrysis (phlebotumurus spp.), brevibacterus (nodestrus spp.), muscathrix (rhinus spp.), muscat-fly (Sarcophaga spp.), musulus (Simulus spp.), muscat-fly (Sarcophaga spp.), simulus spp.), genus (Simulum spp.), genus (Stoxmosys spp.), sp-fly spp., wilmopys spp., tanuus spp., tachys spp., musca-fly (Willias spp.), and Musca-fly (Lepidium spp.);
Arthropods from the order Siphonapterida (siphunapterida), such as the genera Ceratophyllus (Ceratophyllus spp.), ctenocephalides (Ctenocephalides spp.), siphonaptera (Pulex spp.), daphnia (Tunga spp.), and daphnia (Xenopsylla spp.);
arthropods from the order heteroptera (heteropterida), such as the genus bedbug (Cimex spp.), the genus lygus (panstingylus spp.), the genus rhynchophorina (Rhodnius spp.), the genus lygus (Triatoma spp.); and nuisance (nuisance) and sanitary pests from the order blattaria (Blattarida).
Furthermore, as arthropods, by way of example and without limitation, the following Acari subclasses (Acari) should be mentioned:
arthropods from the subclasses Acarina (Acarina) and the phylum Metastigmata (Metastigmaa), such as the family Cryptorhynchophoraceae (Argasidae), such as the genus Iridaceae (Argas spp.), the genus Iridaceae (Ornithodoros spp.), the genus Otobius (Otobius spp.), the family Iridaceae (Ixodidae), such as the genus Iridaceae (Amblyomma spp.), the genus Dermacentor spp.), the genus Haemaphysalis (Haemaphysalis spp.), the genus Iridaceae (Hyalomma spp.), the genus Ixodes (Ixodes spp.), the genus Rhipicephalus (Bombycis spp.), the genus Rhipicephalus (Rhipicephalus spp.); arthropods from the order of the central aerothrida (Mesotrigmata), such as Dermanyssus spp., (Ornithonyssus spp.), dermanyssus spp. (Ornithonyssus spp.), pneumonysus spp.), dermanyssus spp. (Raillietia spp.), dermanyssus spp. (Sternostoma spp.), thermopsis spp.), and Wakawara spp. (Varroa spp.); arthropods from the order of the radiometales (actinodida) (protovalvales), such as, for example, the genera fagaconis (Acarapis spp.), acanthomonas (cheyleteiella spp.), demodex (Demodex spp.), listerphorus spp., sarcophagus (Myobia spp.), neotsutsugamushi (Neotrombicula spp.), chelidonychus (ornithocostia spp.), cyromycetes (psoralens spp.), cyromycetes (sorerbates spp.); and arthropods from the order of the aleyrodida (acarida) (astregmata), such as the genus dermatophagoides (Acarus spp.), the genus xylophila (Caloglyphus spp.), the genus podophytum (chlorites spp.), the genus cytodite (cytotes spp.), the genus cervicodynia (hyponectes spp.), the genus lumus (Kneminoptes spp.), the genus gallinaceae (Laminosteps spp.), the genus proctophaga (Notoederes spp.), the genus otophytes (otonectes spp.), the genus otophytes (otophytes spp.), the genus Psoroptes (Psoroptes spp.), the genus pterodon (Pterchus spp.), the genus sarcophagostomis (Tyrophagus spp.), the genus sarcophagus (Tyrophagus spp.).
Examples of parasitic protozoa include, but are not limited to:
the class of flagellates (Mastigophora) (class of flagellates (Flagelata)), for example:
rear drop door (Metamonada): from the order of the Diplonodida (Diplonodida), for example Giardia (Giardia spp.), dinoflagellate (Spironucleus spp.).
Class submatrix (parakasala): trichomonas (Trichomonodida), for example, trichomonas (Histomonas spp.), trichomonas (Pentatrichomonas spp.), trichomonas (Tetratrichomonas spp.), trichomonas (Trichomonas spp.), and Trichomonas (Trichomonas spp.).
Euglenozoa (Euglenozoa): trypanosomatida (Trypanosomatida), for example, leishmania spp.
The subphylum carnosomiae (sarcophaga) (Rhizopoda) is for example entamoebraceae (entamoebraceae), such as the genera entomoebae (Entamoeba spp.), ceramomediae, such as Acanthamoeba (Acanthamoeba sp.), euamoebidee, such as the genus hamella (hartmarella sp.).
Vesicular insects (Alveolata) such as apotheca (Apicomplexa) (sporozoites (sponozoa)): such as the genus Cryptosporidium (Cryptosporidium spp.); from the order of the Eimeriales (Eimeris), for example, the genera Benoridia (Besnoitia spp.), eimeria (Cystoispora spp.), eimeria (Eimeria spp.), hammond (Hammondia spp.), isospora (Isospora spp.), neospora (Neospora spp.), sarcocystis (Sarcocystis spp.), toxoplasma (Toxoplasma spp.); order adeeida, e.g. the genus ceropus (hepatozon spp.), closeira (Klossiella spp.); from the order of the Haemosporida (Haemosporida), for example the genus Penicillium (Leucocytozon spp.), plasmodium (Plasmodium spp.); from the order of the Piroplasma (Piroplasma), such as Babesia spp, ciliate (Ciliophora spp.), echinozon spp, theileria spp; from the order Vesibuliferida, for example, the genera Enterobacter (Ballantidium spp.), buxton ciliate (Buxtonella spp.).
Microsporidia (Microspora), such as Encephalitozoon (Encephalitozoon spp.), enterospora (enterocytozon spp.), coccidia (Globidium spp.), microsporidia (Nosema spp.), and myxozoon (Myxozoa spp.).
Helminths which are pathogenic to humans or animals include, for example, the phylum Acanthocephala (Acanthocephala), nematodes (nematodies), the phylum hyoglossoides (Pentastoma) and the phylum Platyhelminthes (e.g. monozoea, cestodes and trematodes).
Exemplary worms include, but are not limited to:
monogenea (Monogenea): for example: dactylogyrus spp, gyrocobacter spp, microbothrium spp, plectropodium spp, and troglelecephalus spp;
the tapeworms comprise: tapeworm from the order pseudophyllales (pseudophyllodea), for example: trematopsis (Bothridium spp.), schizocephala (Dipylobotrys spp.), large-reproducing-pore tapeworm (Dipylogonophorus spp.), ichthyothrix spp, ligularia (Ligula spp.), schizocephala (Schistocephalus spp.), and Ectoides (Spirometera spp.).
Tapeworm from the order of the circular phyllales (cyclophyllda), for example: andyra spp, anomala spp (anomala spp.), vitellogenin spp (Avitellina spp.), bert tapeworm spp (berthiella spp.), sycamole tapeworm (citteal spp.), sytemesis spp (citritania spp.), dactylene tapeworm (davaine spp.), dicchondina spp (Diorchis spp.), dipylococcum spp, echinoderma (Echinococcus spp.), echinoderm spp, echinodermata (echinoderm spp.), echinoderma spp., ectodermonetia spp., hymenothecolobium (hylatella spp.), hymenospora (hymenospora spp.), euthecolobium tapetum (hymenospora spp.), pelothrix spp (hymenospora spp.), pelaginospora spp., entada (hymenospora spp.), pelaginospora spp., entamoelleta (setaria spp.), pelaginospora spp.), pellicia (hymenospora spp.), metazoa spp.), and setaria (metazoa spp.).
And (3) sucking insects: flukes from the class of the reproduction (Digenea), for example: <xnotran> (Austrobilharzia spp.), (Brachylaima spp.), (Calicophoron spp.), (Catatropis spp.), (Clonorchis spp.), (Collyriclum spp.), (Cotylophoron spp.), (Cyclocoelum spp.), (Dicrocoelium spp.), (Diplostomum spp.), (Echinochasmus spp.), (Echinoparyphium spp.), (Echinostoma spp.), (Eurytrema spp.), (Fasciola spp.), fasciolides spp., (Fasciolopsis spp.), (Fischoederius spp.), (Gastrothylacus spp.), (Gigantobilharzia spp.), (Gigantocotyle spp.), (Heterophyes spp.), (Hypoderaeum spp.), (Leucochloridium spp.), (Metagonimus spp.), (Metorchis spp.), (Nanophyetus spp.), (Notocotylus spp.), (Opisthorchis spp.), (Ornithobilharzia spp.), (Paragonimus spp.), (Paramphistomum spp.), (Plagiorchis spp.), (Posthodiplostomum spp.), (Prosthogonimus spp.), (Schistosoma spp.), (Trichobilharzia spp.), (Troglotrema spp.), </xnotran> Caecum (Typhlocoelum spp.).
Nematodes: nematodes from the order trichodermales (trichonelida), for example: capillaris (Capillaria spp.), trichinella (Trichinella spp.), trichosporoides spp.
Nematodes from the order of the phylum basichida (Tylenchida), such as: silurus (Micronema spp.), parastrongyloides spp, strongyloides spp.
Nematodes from the order rhabditis (rhabditis), for example: strongyloides felis (Aerostrongylus spp.), heterodera (Amidostomum spp.), heterodera (Trichostomum spp.), ancyloides (Ancylostoma spp.), heterodera (Angiostrongylus spp.), bronchonema spp., butyrospermum spp.), heterodera (Bunostomum spp.), charbertia spp., cupressus spp., cooperiplophora (Cooperita spp.), cooperipheriides spp., cyclo nematode (Crenosoma spp.), coopium spp.), coopimarioides spp. Genus Cyathostomus (Cyathostomum spp.), cyclocercus spp, cyclodotostomum spp, cyclocerus spp (Cyclocerus spp.), cyrosthornus spp (Cyrosthornus spp.), cylindrochanus spp (Cylindrochanus spp.), dictyocaulus spp (Dictyocaulus spp.), and Dictyocola spp (Elaphanophys spp.) filarioid (fililioids spp.), globulus sp, graphalitus spp, rhabdoid (globococculus spp.), hematonchus spp, heliotropium spp, trichosanthes spp (hystrocaryus spp.), marshallus spp, strongyloides (marshallia spp.), strongyloides (metastrocaryus spp.), mullerus (Muellerius spp.), ostertagia spp (neustonus spp.), ostertagia spp, necator (neustonia spp.), necator spp, nematodiasis (neustonus spp.), necator (neustonus spp.), nematodiasis spp, neostrongyloides (neonematodirus spp.), necator (neustonus spp.), necator spp, ostertagia spp, esophagostyloides (obesus spp.), oesophagus spp.); ornithostrongylus spp, oslerus spp, osletaria spp, ostera spp, paraconidia spp, parachrysoidea spp, pararhabdomyopterus spp, pneumocolus spp, pneumothrix spp, pneumotromostomus spp, poteriostomum spp, prorocentrum spp, and Ostrematongylus spp Ceratoptera spp, coprinus spp, stropharuus spp, stropharyngyloides spp, strongyloides spp, syngamus spp, stradoragus spp, trichinella spp, cryptostrongyloides spp, and Uncaria spp.
Nematodes from the order of the gyroda (Spirurida), for example: acanthocheilonema spp, anisakis spp, ascaris galli spp; ascaris (Ascaris spp.), acarpous (Ascaris spp.), acanthosis (asciplus spp.), ascaris (bayliscas spp.), bruxism (Brugia spp.), cercopicus spp., crassicauliflora spp., bivalvular nematoma spp., dirofilaria (diptera spp.), dirofilaria spp., and trichina (Dracrucuus spp.); draschia spp, pinworm (Enterobius spp.), filaria (Filaria spp.), ostertagia (Glyata spp.), ostertagia (Gnathostoma spp.), cylindrocarpon (Gongylonema spp.), lithothamus (Habronema spp.), and Heterotrichum (Heterakis spp.); smooth-haired-worm-like genus (litomosoids spp.), luoshi (Loa spp.), disc-tail-haired-worm (Onchocerca spp.), cuneathe (Oxyuris spp.), parabacting-worm (pararonema spp.), paraphenylworm (paraalaria spp.), paraphenylworm (paracaris spp.), cocardia paraphenylworm (paracaris spp.), embolus (miseranus spp.), echinococcus spp.), kytophus spp., picula (paracaris spp.), kytophus spp.), pterodon (physalopilus spp.), prosperous spp., prothallicia spp., eudaofilia spp., celastrus spp., setaria spp., skjrabaeum spp., spiracle tail-worm (spirococcus spp.), crown-worm (stenoptera spp.), cophaga straussp, stenoptera spodopsis spp.), euplophora (stenoptera spp.), euplophora stylosis spp.), euplophora stenoptera (stenoptera spp.), euplophora spp.).
Acanthocephala (Acanthocephala): the order of Chimonaria (Oligacanthahythida), for example: echinocandis megalossus spp, epididymis spp; the order of candida (Moniliformida), for example: the genus Echinoderma Moniliformis (Moniliformes spp.).
Orders of multiformes (Polymorphida), for example: genus stenocardia (filicolis spp.); the order Echinochida (Echinorhynchida), for example, echinacea (Acanthocephalus spp.), echinopsis (Echinorhynchus spp.), echinococcus tenuifolius (Leptophynchoides spp.).
Tongue-shaped animal gate: from the order of the phylum Toxoviridae (Porocephalida), for example, the genus Toxoviridae (Linguatula spp.).
In the veterinary field and in animal husbandry, the compounds of formula (I) are administered in the form of suitable formulations by methods generally known in the art, such as enterally, parenterally, dermally or nasally. Administration may be prophylactic, remedial (methylactic) or therapeutic.
Accordingly, one embodiment of the present invention relates to compounds of formula (I) for use as medicaments.
Another aspect relates to compounds of formula (I) for use as anti-endoparasitic agents.
Another particular aspect of the invention relates to the use of a compound of formula (I) as anthelmintic agent, in particular as nematicide, flatting agent (platystelminticide), echinodeicide (acanthocephalide) or glossocide (pentastomide).
Another particular aspect of the invention relates to the use of a compound of formula (I) as an antiprotozoic agent.
A further aspect relates to the use of a compound of formula (I) as an antiparasitic agent, especially an arthropodicide, very particularly an insecticide or acaricide.
Other aspects of the invention are veterinary formulations comprising an effective amount of at least one compound of formula (I) and at least one of the following: a pharmaceutically acceptable excipient (e.g. a solid or liquid diluent), a pharmaceutically acceptable adjuvant (e.g. a surfactant), particularly a pharmaceutically acceptable excipient typically used in veterinary formulations and/or a pharmaceutically acceptable adjuvant typically used in veterinary formulations.
A related aspect of the invention is a process for the preparation of a veterinary formulation as described herein, comprising the step of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and/or adjuvants, in particular with pharmaceutically acceptable excipients and/or adjuvants conventionally used in veterinary formulations.
Another particular aspect of the invention is a veterinary preparation selected from the ectoparasiticidal and endoparasiticidal preparations of the mentioned aspect, in particular from the group consisting of anthelmintic, antiprotozoal and arthropodicidal preparations, very particularly from the group consisting of nematicidal, platyhelminthidal, echinoderm (echinocandial), lingual (pentamicial), insecticidal and acaricidal preparations, and a process for its preparation.
Another aspect relates to a method of treating a parasitic infection, in particular an infection caused by a parasite selected from the group consisting of an ectoparasite and an endoparasite mentioned herein, by using an effective amount of a compound of formula (I) in an animal, in particular a non-human animal, in need thereof.
Another aspect relates to a method of treating a parasitic infection, in particular an infection caused by a parasite selected from the group consisting of an ectoparasite and an endoparasite mentioned herein, by using a veterinary formulation as defined herein in an animal, in particular a non-human animal, in need thereof.
Another aspect relates to the use of a compound of formula (I) for the treatment of a parasitic infection in an animal, in particular a non-human animal, in particular an infection caused by a parasite selected from the group consisting of an ectoparasite and an endoparasite mentioned herein.
In the context of animal health or veterinary medicine of the present invention, the term "treatment" includes prophylactic, remedial and therapeutic treatments.
In a particular embodiment, the method is used to provide a mixture of at least one compound of formula (I) with other active ingredients, in particular with endoparasiticides and ectoparasiticides, for the veterinary field.
In the field of animal health, "mixture" not only means that two (or more) different active ingredients are formulated in a common formulation and used together accordingly, but also relates to a product comprising separate formulations of the active ingredients. Thus, when more than two active ingredients are used, all of the active ingredients may be formulated in a common formulation or all of the active ingredients may be formulated in separate formulations; also possible are mixed forms: some of which are formulated together and some of which are formulated separately. The separate formulations allow for separate or sequential administration of the active ingredients.
The active ingredients specified herein under their "common names" are known and described, for example, in "Pesticide Manual" (see above) or may be available on the internet (for example:http://www.alanwood.net/pesticides) And (4) retrieving.
Exemplary active ingredients from ectoparasiticides as mixed components include, without any intention to be construed as limiting, the insecticides and acaricides listed in detail above. According to the above classification based on the current IRAC mode of action classification scheme, the following list other active ingredients that can be used: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-gated chloride channel blockers; (3) sodium channel modulators; (4) nicotinic acetylcholine receptor (nAChR) competitive modulators; (5) nicotinic acetylcholine receptor (nAChR) allosteric modulators; (6) Glutamate-gated chloride channel (GluCl) allosteric modulators; (7) juvenile hormone mimics; (8) other non-specific (multi-site) inhibitors; (9) chord tone organ modulators; (10) mite growth inhibitors; (12) mitochondrial ATP synthase inhibitors, such as ATP disruptors; (13) An uncoupler of oxidative phosphorylation by an interrupted proton gradient; (14) nicotinic acetylcholine receptor channel blockers; (15) type 0 chitin biosynthesis inhibitors; (16) type 1 chitin biosynthesis inhibitors; (17) molt disruptors (especially in diptera); (18) ecdysone receptor agonists; (19) octopamine receptor agonists; (21) mitochondrial complex I electron transport inhibitors; (25) mitochondrial complex II electron transport inhibitors; (20) mitochondrial complex III electron transport inhibitors; (22) voltage-dependent sodium channel blockers; (23) inhibitors of acetyl-coenzyme a (CoA) carboxylase; (28) ryanodine (ryanodine) receptor modulators;
Active ingredients with an unknown or unspecific mechanism of action, such as nitrofluranilide (fentrifanil), oxapyrimide (fenoxacrim), cycloprene, dicofol (chlorobenzilate), chlordimeform (chloroformim), fluben (flubenizin), dicyclanil (dicyclanil), sulfamite (amidoflumate), merfenmanate (quinomethionate), chlorfenadine (triarthhene), clothiazoben, dicofol (tetrasul), potassium oleate, petroleum, methoxazone (methoxazone), gossyplur, flufenzine (flutenzine), bromopropylate (bropromylpyrate), cryolite;
a compound selected from the group consisting of other classes, for example, live animal dung or insects, such as, for example, busulfan, dichlorcarb, cloethocarb, phosmet, pirimiphos-ethyl, parathion, chlorfenvinphos, isopropyl o-salicylate, trichlorfon, thiopropyl, prophos, fenamiphos, thiobencarb, pyridaphenthion, thiophanate, dichlorphos, and thiophosphorum, demeton-S-methyl sulfonate chlorazol-phos (isozofos), cyanophosphine (cyanofenofos), chlorophosphine (dialfoss), thiophosphorous (carbophenothion), autathionos, aromfenvinfos (-methyl), oryzophos (azinphos (-ethyl)), chlorpyrifos (-ethyl)), butathion (fosetyl), iodophos (iodofenphos), dicofos (dioxabenzofos), formothion (formothion), fonofos (fonofos), fluoxathion (flupyrazofos), sulophos (fenthion), ethirimos (ethimfos);
Organochlorine compounds, such as toxaphene (camphechlorir), lindane (lindane), heptachlor (heptachlor); or phenylpyrazoles, such as acetoprole (acetoprole), pyrafluprole, pyriprole, fluoropyrazole (vanilprole), virginiamycin (sisapronil); or isoxazolines, such as sarolaner, alfolaner (afoxolaner), lotilaner, fluralaner (fluralaner);
pyrethroids (pyrethroids), such as (cis-, trans-) metofluthrin (methofluthrin), proffluthrin (profluthrin), trifloxystrobin (flufenprox), fluthrin (flubiscycyclinate), fubfenprox, pentafluorothrin (fenfluthrin), protrifenbut, pyrethroids (pyrethrin), RU15525, cyclopentene (terethrin), cis-resmethrin (cis-resmethrin), heptafluthrin, bioethrin (bioperfluthrin), bifenthrin (bioperfluthrin), fenpyrathrin (fenpyrarithrin), cis-cypermethrin (cis-cypermethrin), cis-permethrin (cis-permethrin), cyhalothrin (cyhalothrin), lambda-cyhalothrin (HCL, HCL H) or Halothrin (HCL),
neonicotinoids (neonicotinoids), for example nithiazine
diclomezotiaz, trifluoropyrimidine (triflumzopyrim)
Macrolides such as nemadectin (nemadectin), ivermectin (ivermectin), latidectin (latidectin), moxidectin (moxidectin), selamectin (selamectin), eprinomectin (eprinomectin), doramectin (doramectin), emamectin benzoate (emamectin benzoate); milbemycin oxime (milbemycin oxime)
Methoprene (triprene), juvenile ether (eponenane), bendiofenolan (diofenolan);
biologicals, hormones or pheromones, e.g. natural products, e.g. components of thuringiensis, dodecadienol or neem
Dinitrophenols such as dinocap (dinocap), dicroton (dinobuton), binacryl (binacryl);
benzoylureas, such as, for example, fluazuron (fluzuron), chlorfluazuron (penfluron),
amidine derivatives, e.g. chloronebuform, acarine (cymiazole), dimidiate (demiritraz)
Varroa miticides (beehive varroa acarcicides) such as organic acids, e.g. formic acid, oxalic acid.
Exemplary active ingredients from the group of endoparasiticides as mixed components include, but are not limited to, anthelmintic and antiprotozoal active ingredients.
Anthelmintic active ingredients include, but are not limited to, the following nematicidal, trematocidal and/or cestocidal active ingredients:
from the class of macrolides, for example: eprinomectin (epidemicin), abamectin (abamectin), nemadectin (nemadectin), moxidectin (moxidectin), doramectin (doramectin), selamectin (selamectin), lepimectin (lepimectin), latidecctin (latidecctin), milbemectin (milbemectin), ivermectin (ivermectin), emamectin (emamectin), milbemycin (milbemycin);
from benzimidazoles and probenzimidazoles, for example: oxibendazole (oxibendazole), mebendazole (mebendazole), triclabendazole (triclabendazole), thiophanate (thiophanate), pamezole (parbendazole), oxfendazole (oxibendazole), netobimin (netobimin), fenbendazole (fenbendazole), fenoxanil (febantel), thiabendazole (thiabendazole), cyclobendazole (cyclobendazole), cambendazole (cambendazole), albendazole sulfoxide (albendazole), albendazole (albendazole), flubendazole (flabendazole);
from depsipeptides (depsipeptides), preferably cyclic depsipeptides, in particular 24-membered cyclic depsipeptides, such as: emodepside, PF1022A;
From the class of tetrahydropyrimidines, for example: morantel (morantel), pyrantel (pyrantel), octotan (oxantel);
from the class of imidazothiazoles, for example: butylimidazole (butamisole), levamisole (levamisole), tetraimidazole (tetramisole);
from the class of aminophenylamidines, for example: amitripter (amidintel), deacylated amitripter (dAMD), triphenyldiamidine (tribenzimine);
from the class of aminoacetonitriles, for example: monentael (monepantel);
from paraherquamides, for example: paraherquamide, deletrent (derqualel);
from the class of salicylanilides (salicinilides), for example: tribromosalan (tribromosalan), bromxanide (bromoxide), brotinide (brotinide), cloiodoxanide (cloxanide), closantel (closantel), niclosamide (nilosamide), oxyclozanide (oxyclozanide), and rafoxanide (rafoxanide);
from substituted phenols, for example: nitroiodophenol nitrile (nitroxynil), thiochlorophenol (bithionol), diiodonitrophenol (disphenol), hexachlorophene (hexachlorophene), nitrochlorophenol (nicolfolan), menicophoran;
from the class of organophosphates, for example: trichloro phosphate (trichlorfon), naphthalofos, dichlorvos/DDVP, foster phosphorus (crufomate), coumaphos (coumaphos), haloxon (haloxon);
From piperazinones/quinolines, for example: praziquantel (praziquantel), epsiprantel (epsilon prantel);
from the piperazines, for example: piperazine, hydroxyzine;
from the tetracyclines, for example: tetracycline (tetracycline), chlorotetracycline (chlorotetracycline), doxycycline (doxycycline), oxytetracycline (oxytetracycline), and rolicycline (rolitecycline);
from various other classes, for example: bunamidine (bunamidine), nilidazole (niridazole), resorcinol (resorantel), omphalitin, oltipraz (oltipraz), nitrothiocyanate (nitroscanate), nitrolotil (nitroxynil), oxaniquine (oxamniquin), mirasan, lucamine hydrochloride (miracil), lucanthone (lucanthon), hyantone (hycanthonon), pitorin (hetolin), emetin (emetin), diethylcarbamazine (diethylcarbamazine), diclofenac, diphenidine (diamfenetide), clonazepam (clonazepam), phenenium (phenoxide), nitrocyanamide (amosulosin), clorsulon (clorsulon).
Antiprotozoal active ingredients include, but are not limited to, the following active ingredients:
from the class of triazines, for example: diclazuril (diclazuril), ponazuril (ponazuril), letrazuril (letrazuril), toltrazuril (toltrazuril);
From the class of polyether ionophores, for example: monensin (monensin), salinomycin (salinomycin), maduramicin (maduramicin), narasin (narasin);
from the class of macrolides, for example: milbemycins, erythromycins, and erythromycin;
from quinolones, for example: enrofloxacin (enrofloxacin), pradofloxacin (pradofloxacin);
from the class of quinines, for example: chloroquine (chloroquine);
from the pyrimidines, for example: pyrimethamine (pyrimethamine);
from the sulfonamides, for example: sulfaquinoxaline, trimethoprim, sulfaclozine;
from the class of thiamines, for example: amproline (amprolium);
from the lincosamides (lincosamides), for example: clindamycin (clindamycin);
from carboxanilides, for example: a mimidocabs (imidocarb);
from the class of nitrofurans, for example: nifurtimox (nifurtimox);
from quinazolinone alkaloids, for example: halofuginone (halofuginone);
from various other classes, for example: oxanil (oxamniquin), paromomycin (paromomycin);
from microbial vaccines or antigens, for example: babesia robusta subspecies (Babesia canis rossi), eimeria tenella (Eimeria tenella), eimeria praecox (Eimeria praecox), eimeria necatrix (Eimeria necatrix), and Eimeria mitis (Eimeria mitis), eimeria maxima (Eimeria maxima), eimeria brunetti (Eimeria brunetti), eimeria acervulina (Eimeria acervulina), babesia westermanis subspecies (Babesia canis voli), leishmania infantis (Leishmania infantum), babesia canis subspecies (Babesia canis), and Nephila foetida (Dictyocaulus viensis).
If, as the case may be, all the mixed components mentioned are capable of forming salts with suitable bases or acids on the basis of their functional groups, they may also form salts with suitable bases or acids.
Vector control
The compounds of formula (I) may also be used for vector control. In the context of the present invention, vectors are arthropods, in particular insects or arachnids, which are capable of transmitting pathogens (e.g. viruses, worms, unicellular organisms and bacteria) from a reservoir (reservoir) (plant, animal, human, etc.) to a host. The pathogen may be transmitted to the host mechanically (e.g., a trachoma transmitted by a non-biting fly) or after injection (e.g., a plasmodium transmitted by a mosquito).
Examples of vectors and their transmitted diseases or pathogens are:
1) Mosquito eradication device
-anopheles mosquito: malaria, filariasis;
-culex: japanese encephalitis, filariasis, other viral diseases, spread of other worms;
-aedes: yellow fever, dengue fever, other viral diseases, filariasis;
-gnathoceae (simuloidae): spread of worms, particularly the circumflex volvulus (Onchocerca volvulus);
-family trichothecaceae (Psychodidae): leishmaniasis transmission
2) Lice: skin infection, epidemic typhus fever;
3) Fleas: plague, endemic typhus, cestodes;
4) Fly: narcolepsy (trypanosomiasis); cholera, other bacterial diseases;
5) Mite: acariasis, epidemic typhus, rickettsia pox, tularemia, st-lewis encephalitis, tick-borne encephalitis (TBE), crimian-Congo haemic fever (Crimean-Congo haemrogic feber), borreliosis (borreliosis);
6): tick: borelliosis, such as Borrelia burgdorferi (Borrelia burgdorferi sensu lato.), borrelia dorferi (Borrelia duttoni), tick-borne encephalitis, Q fever (Coxiella burnetii), babesia disease (babesia) (Babesia canis subsp.), ehrlichiosis (ehrlichiosis).
In the context of the present invention, examples of vectors are insects which can transmit plant viruses to plants, such as aphids, flies, leafhoppers or thrips. Other vectors capable of transmitting plant viruses are spider mites, lice, beetles and nematodes.
In the context of the present invention, further examples of vectors are insects and arachnids such as mosquitoes, in particular of the genus aedes, anopheles, for example anopheles gambiae (a. Gambiae), anopheles arabica (a. Arabienis), anopheles funestus (a. Funestus), anopheles macrorrhalis (a. Malaria) and culex species, which can transmit pathogens to animals and/or humans; family mucocidae (Psychodidae) such as genus chrysopa (phlebotomics), genus chrysopa (lutzomya); lice; fleas; flies; mites and ticks.
If the compounds of the formula (I) are resistance-breaking, vector control is also possible.
The compounds of formula (I) are suitable for the prevention of diseases and/or pathogens transmitted by vectors. Thus, a further aspect of the invention is the use of compounds of formula (I) for vector control, for example in agriculture, horticulture, forestry, gardens and leisure facilities, and in the protection of materials and stored products.
Industrial material protection
The compounds of formula (I) are suitable for protecting industrial materials from attack or destruction by insects from, for example, the orders Coleoptera (Coleoptera), hymenoptera (Hymenoptera), isoptera (Isoptera), lepidoptera (Lepidoptera), rodentia (pseudoptera) and chlamydomonas (zygenoma).
In the context of the present invention, industrial materials are understood to mean inanimate materials, such as preferably plastics, adhesives, binders, paper and card, leather, wood, processed wood products and coating compositions. The use of the invention for protecting wood is particularly preferred.
In another embodiment, the compounds of formula (I) are used together with at least one other insecticide and/or at least one fungicide.
In another embodiment, the compound of formula (I) is in the form of a ready-to-use pesticide, meaning that it can be used without further modification in the material. Useful other insecticides or fungicides include in particular those mentioned above.
Surprisingly, it has also been found that the compounds of formula (I) can be used to protect objects which come into contact with salt or brackish water, in particular ship hulls, screens, nets, buildings, moorings and signalling systems, from fouling. Likewise, the compounds of formula (I) can be used as anti-fouling compositions, alone or in combination with other active ingredients.
Control of animal pests in the hygiene field
The compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector. More particularly, the invention can be used in the field of household protection, hygiene protection and protection of stored products, in particular for controlling insects, arachnids, ticks and mites encountered in enclosed spaces (e.g. houses, factory workshops, offices, vehicle cabins, animal keeping facilities). For controlling animal pests, the compounds of the formula (I) are used alone or in combination with other active ingredients and/or auxiliaries. It is preferably used in domestic pesticide products. The compounds of formula (I) are effective against sensitive and resistant species and against all developmental stages.
These pests include, for example, the following: arachnida (Arachnida), scorpions (Scorpiones), arachnids (Araneae) and cecostomys (opinions); labiatae (Chilopoda) and bypoda (Diplopoda); the orders of the Insecta Blattaria (Blattodea), coleoptera (Coleoptera), dermaptera (Dermaptera), diptera (Diptera), heteroptera (Heteroptera), hymenoptera (Hymenoptera), isoptera (Isoptera), lepidoptera (Lepidoptera), anoplura (Phthiraptera), rodentia (Psocoptera), ptotaria (Saltoraria) or Orthoptera (Orthoptera), siphonaptera (Siphonaptera) and Chlamydomona (Zygentoma); and the order Isopoda (Isopoda) of the class Tetranychus (Malacostraca).
For example, the application is carried out in the following manner: in aerosols, pressureless spray products (e.g. pump sprays and nebuliser sprays), automatic fogging systems, sprays, foams, gels, evaporation products with evaporation tablets made of cellulose or plastics (evaprorator tablets), liquid evaporators, gel and film evaporators, propeller-driven evaporators, unpowered or passive evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in bait or bait stations (baitstation) for broadcasting.
Preparation examples
2-bromo-1-methyl-1H-imidazole-4-carboxylic acid ethyl ester
Figure GDA0003969167050001081
30g (193.5 mmol) of ethyl 1-methyl-1H-imidazole-4-carboxylate are dissolved in 500ml of tetrahydrofuran and cooled to 0 ℃. To this solution, 34.5g (193.5 mmol) of NBS was added in small portions and the reaction mixture was stirred at room temperature overnight. By adding saturated sodium thiosulfate solution (Na) 2 S 2 O 3 ) The reaction was terminated and 800ml ethyl acetate was added. The phases are separated and the aqueous phase is extracted 3 times with 800ml of ethyl acetate each time. The organic phases were combined, dried over sodium sulfate and filtered. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography using a petroleum ether/ethyl acetate gradient as mobile phase.
1 H-NMR(300MHz,D6-DMSO)δppm:1.26(t,3H),3.64(s,3H),4.22(q,2H),8.07(s,1H)。
1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazole-4-carboxylic acid ethyl ester
Figure GDA0003969167050001091
To a solution of 10g (43.1 mmol) of ethyl 2-bromo-1-methyl-1H-imidazole-4-carboxylate in 1, 2-dimethoxyethane (30 ml) and water (10 ml) were added 3.2g (4.4 mmol) of tetrakis (triphenylphosphine) palladium, 9.1g (85.8 mmol) of sodium carbonate and 16.4g (86.3 mmol) of (4-trifluoromethyl) phenylboronic acid under a nitrogen atmosphere. The reaction mixture was stirred at 80 ℃ overnight. The mixture was then cooled to room temperature and extracted twice with 100ml of ethyl acetate each time. The organic phases were combined, dried over sodium sulfate and filtered. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography using a petroleum ether/ethyl acetate gradient as mobile phase.
1 H-NMR(300MHz,D6-DMSO)δppm:1.28(t,3H),3.85(s,3H),4.25(q,2H),7.86-7.89(m,2H),7.97-8.00(m,2H),8.09(s,1H)。
5-iodo-1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazole-4-carboxylic acid ethyl ester
Figure GDA0003969167050001092
To a solution of 5.2g (17.4 mmol) of ethyl 1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazole-4-carboxylate in acetic acid (20 ml) was added 7.9g (35.1 mmol) of N-iodosuccinimide (NIS). The reaction mixture was stirred at room temperature overnight. The mixture was then concentrated under reduced pressure and diluted by addition of saturated sodium thiosulfate solution. The pH was adjusted to pH =7-8 by adding saturated sodium carbonate solution. The mixture was then extracted with ethyl acetate. The organic phases were combined, dried over sodium sulfate and filtered. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography using a petroleum ether/ethyl acetate gradient as mobile phase.
1 H-NMR(300MHz,D6-DMSO)δppm:1.31(t,3H),3.74(s,3H),4.27(q,2H),7.85-7.95(m,4H)。
5- (ethylsulfanyl) -1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazole-4-carboxylic acid ethyl ester
Figure GDA0003969167050001101
To a solution of 4.1g (9.7 mmol) of 5-iodo-1-methyl-2- [4- (trifluoromethyl) phenyl ] carbonyl]To a solution of ethyl (E) -1H-imidazole-4-carboxylate in 1, 4-dioxane (150 ml) were added 6.0g (96.7 mmol) of ethanethiol, 2.9g (29.0 mmol) of N, N-Diisopropylethylamine (DIPEA), 1.5g (1.5 mmol) of tris (dibenzylideneacetone) dipalladium (0) -chloroform adduct [ Pd2 (dba) 3 ·CHCl 3 ]And 1.7g (2.9 mmol) of Xantphos. The mixture was stirred at 80 ℃ overnight. Subsequently, the reaction mixture was cooled to room temperature, and water was added to the mixture. The mixture was then extracted twice with ethyl acetate. The organic phases were combined, dried over sodium sulfate and filtered. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography using a petroleum ether/ethyl acetate gradient as mobile phase.
1 H-NMR(300MHz,D6-DMSO)δppm:1.15(t,3H),1.31(t,3H),2.92(q,2H),3.80(s,3H),4.28(q,2H),7.88-7.99(m,4H)。
5- (ethylsulfanyl) -1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazole-4-carboxylic acid
Figure GDA0003969167050001102
To a solution of 3.1g (8.7 mmol) of ethyl 5- (ethylsulfanyl) -1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazole-4-carboxylate in methanol (60 ml) and water (60 ml) was added 0.69g (17.3 mmol) of sodium hydroxide. The mixture was stirred at room temperature overnight. The solution was adjusted to pH =3-4 by adding concentrated aqueous hydrochloric acid. The reaction mixture was then extracted with a mixture of chloroform/isopropanol (3. The organic phases were combined, dried over sodium sulfate and filtered. The solvent was distilled off under reduced pressure and the residue was used without further purification in the next synthesis step.
{5- (ethylsulfanyl) -1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazol-4-yl } carbamic acid tert-butyl ester
Figure GDA0003969167050001111
To a solution of 3.6g (10.9 mmol) of 5- (ethylthio) -1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazole-4-carboxylic acid in tert-butanol (60 ml) were added 4.5g (16.4 mmol) of Diphenylphosphorylazide (DPPA) and 3.9g (38.2 mmol) of triethylamine. The mixture was stirred at 80 ℃ overnight, cooled and concentrated under reduced pressure. Then 100ml of water was added and the mixture was extracted with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using an ethyl acetate/petroleum ether gradient as eluent.
1 H-NMR(300MHz,D6-DMSO)δppm:1.15(t,3H),1.44(s,9H),2.72(q,2H),3.79(s,3H),7.85-7.96(m,4H),8.65(s,1H)。
5- (ethylsulfanyl) -1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazol-4-amine
Figure GDA0003969167050001112
To a solution of 2.4g (6.0 mmol) of tert-butyl {5- (ethylsulfanyl) -1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazol-4-yl } carbamate in dioxane (40 ml) was added 40ml of concentrated hydrochloric acid. The mixture was stirred at room temperature overnight and then concentrated to dryness under reduced pressure. The crude product was used without further purification.
1 H-NMR (300MHz, D6-DMSO). Delta.ppm 1.15 (t, 3H), 2.58 (q, 2H), 3.68 (s, 3H), 4.81 (s, broad, 2H), 7.80-7.92 (m, 4H).
3-azido-5- (trifluoromethyl) pyridine-2-carbaldehyde
Figure GDA0003969167050001113
First, 1g (5.2 mmol) of 3-fluoro-5- (trifluoromethyl) pyridine-2-carbaldehyde was added to 10ml of Dimethylformamide (DMF) and cooled to 0 ℃. Then, 0.34g (5.2 mmol, dissolved in 10ml of DMF) of sodium azide was added and the mixture was stirred at room temperature for 4h. The reaction was stopped by adding 100ml of water. The mixture is extracted twice with 100ml of ethyl acetate each time. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was used without further purification.
2- {5- (ethylsulfanyl) -1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazol-4-yl } -6- (trifluoromethyl) -2H-pyrazolo [4,3-b ] pyridine
Figure GDA0003969167050001121
To a solution of 200mg (0.66 mmol) 5- (ethylsulfanyl) -1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazol-4-amine in toluene (15 ml) were added 290mg (1.3 mmol) 3-azido-5- (trifluoromethyl) pyridine-2-carbaldehyde and 850mg (2.99 mmol) titanium isopropoxide. The mixture was first stirred at 50 ℃ for 4h and then at 100 ℃ for 1h. After cooling to room temperature, 100ml of water were added, and the mixture was extracted with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using an ethyl acetate/petroleum ether gradient as eluent.
1 H-NMR(300MHz,D6-DMSO)δppm:1.10(t,3H),2.90(q,2H),3.93(s,3H),7.94-7.96(m,2H),8.08-8.11(m,2H),8.82(s,1H),8.91(s,1H),9.34(s,1H)。
2- {5- (ethylsulfonyl) -1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazol-4-yl } -6- (trifluoromethyl) -2H-pyrazolo [4,3-b ] pyridine (I-098)
Figure GDA0003969167050001122
A solution of 130mg (0.28 mmol) 2- {5- (ethylsulfanyl) -1-methyl-2- [4- (trifluoromethyl) phenyl ] -1H-imidazol-4-yl } -6- (trifluoromethyl) -2H-pyrazolo [4,3-b ] pyridine in dichloromethane (20 ml) is cooled to 0 ℃ and 100mg (1.2 mmol, 35% strength in water) of hydrogen peroxide and 100mg (2.9 mmol) of formic acid are added. The mixture was stirred at room temperature for 5h, diluted by the addition of 50ml of dichloromethane and washed with saturated sodium thiosulfate solution and saturated sodium bicarbonate solution. The organic phase was separated, dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was purified by preparative HPLC using a water/acetonitrile gradient as eluent.
1 H-NMR(300MHz,D6-DMSO)δppm:1.33(t,3H),3.79(q,2H),4.00(s,3H),7.98-8.00(m,2H),8.06-8.09(m,2H),8.84(s,1H),8.93(s,1H),9.36(s,1H)。
2-bromo-5- (ethylsulfanyl) -1-methyl-1H-imidazole-4-carboxylic acid
Figure GDA0003969167050001131
31g (134 mmol) of ethyl 2-bromo-1-methyl-1H-imidazole-4-carboxylate and 24.4g (200 mmol) of diethyl disulfide were dissolved in 620ml of tetrahydrofuran and cooled to-78 ℃. To this solution 100ml (2M in THF, 200mmol) of Lithium Diisopropylamide (LDA) were added dropwise and the reaction mixture was stirred at-78 ℃ for 30 min. The reaction was terminated by the addition of saturated ammonium chloride solution. The phases are separated and the aqueous phase is extracted 3 times with 300ml of ethyl acetate each time. The organic phases were combined, dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography using a petroleum ether/ethyl acetate gradient as mobile phase. 28.5g (97.3 mmol) of ethyl 2-bromo-5- (ethylsulfanyl) -1-methyl-1H-imidazole-4-carboxylate are obtained. It was dissolved in 300ml of methanol and the solution was cooled to 0 ℃. 300ml (2N, 600mmol in water) of sodium hydroxide were then added and the mixture was stirred at room temperature for 1h. The mixture was concentrated on a rotary evaporator and neutralized by addition of 1N HCl. The mixture was extracted with ethyl acetate. The solvent was distilled off under reduced pressure to obtain the objective mixture.
1 H-NMR(300MHz,D6-DMSO)δppm:1.09(t,3H),2.86(q,2H),3.64(s,3H),12.60(s,1H)。
2- [ 2-bromo-5- (ethylsulfanyl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-010)
Figure GDA0003969167050001141
To a solution of 9.02g (34.0 mmol) 2-bromo-5- (ethylsulfanyl) -1-methyl-1H-imidazole-4-carboxylic acid in pyridine (50 ml) was added 5.00g (26.1 mmol) N 3 -methyl-6- (trifluoromethyl) pyridine-3, 4-diamine and 5.01g (26.1 mmol) 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI). The mixture was stirred at room temperature for three days. Subsequently, the solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate (50 ml). The mixture was stirred at 100 ℃ for 6h, cooled to room temperature, slurried with water, then filtered through a Nutsche filter and dried to obtain the target compound.
1 H-NMR(400MHz,D6-DMSO)δppm:1.11(t,3H),3.00(q,2H),3.76(s,3H),4.15(s,3H),8.19(s,1H),9.15(s,1H)。
2- [ 2-bromo-5- (ethylsulfonyl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-004)
Figure GDA0003969167050001142
To a solution of 10.3g (24.5 mmol) 2- [ 2-bromo-5- (ethylsulfanyl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine in dichloromethane (100 ml) are added 4.64ml (122 mmol) of formic acid and 15.1ml (172 mmol, 35% strength in water) of hydrogen peroxide. The mixture was stirred at room temperature overnight and the reaction was stopped by the addition of saturated sodium thiosulfate solution. The organic phase was separated, dried over sodium sulfate, and filtered to obtain the objective compound.
1 H-NMR(400MHz,D6-DMSO)δppm:1.27(t,3H),3.74(q,2H),3.92(s,3H),3.96(s,3H),8.24(s,1H),9.22(s,1H)。
2- {2- [ (E) -2-Cyclopropylvinyl ] -5- (ethylsulfonyl) -1-methyl-1H-imidazol-4-yl } -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-007)
Figure GDA0003969167050001151
First, under a protective gas atmosphere, 150mg (0.33 mmol) of 2- [ 2-bromo-5- (ethylsulfonyl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-004), 64.4mg (0.33 mmol) of 2- [ (E) -2-cyclopropylvinyl ] -4, 5-tetramethyl-1, 3, 2-dioxaborolan (dioxaborolan) and 11.5mg (0.01 mmol) of tetrakis (triphenylphosphine) palladium were added. 2.6ml of degassed dioxane and 1.3ml of degassed aqueous sodium carbonate solution (1M) were then added. The mixture was stirred at 92 ℃ overnight. After cooling, the solvent was distilled off under reduced pressure. The residue was dissolved in dichloromethane and washed with water. The organic phase was separated, dried over magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure. The crude product was purified by column chromatography using a cyclohexane/acetone gradient as eluent.
1 H-NMR(400MHz,D6-DMSO)δppm:0.64-0.68(m,2H),0.90-0.95(m,2H),1.24(t,3H),1.73-1.77(m,1H),3.65(q,2H),3.92(s,3H),3.93(s,3H),6.38-6.44(m,1H),6.75(d,1H),8.22(s,1H),9.20(s,1H)。
2- [2- (2-Cyclopropylethyl) -5- (ethylsulfonyl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-085)
Figure GDA0003969167050001152
179mg (0.40 mmol) of 2- {2- [ (E) -2-cyclopropylvinyl ] -5- (ethylsulfonyl) -1-methyl-1H-imidazol-4-yl } -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-007) in 10ml of methanol are initially charged to the autoclave. 50mg (0.04mmol, 10%) palladium on carbon are then added and the mixture is stirred for 16h under a hydrogen atmosphere of 5 bar. After pressure equilibration and removal of the hydrogen atmosphere, the mixture was filtered through celite and the solvent was distilled off under reduced pressure. The crude product was purified by column chromatography using a cyclohexane/acetone gradient as eluent.
1 H-NMR(400MHz,D6-DMSO)δppm:0.04-0.08(m,2H),0.40-0.44(m,2H),0.80-0.85(m,1H),1.26(t,3H),1.64-1.70(m,2H),2.94(t,2H),3.69(q,2H),3.89(s,3H),3.95(s,3H),8.21(s,1H),9.19(s,1H)。
2- [2- (6-Chloropyridin-2-yl) -5- (ethylsulfonyl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-014)
Figure GDA0003969167050001161
200mg (0.44 mmol) 2- [ 2-bromo-5- (ethylsulfonyl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-004), 267mg (0.66 mmol) 2-chloro-6- (tributyltin-yl) pyridine, 56mg (1.32 mmol) lithium chloride, 8mg (0.04 mmol) copper (I) iodide and 102mg (0.08 mmol) tetrakis (triphenylphosphine) palladium are initially charged to degassed dioxane (4 ml) under a protective gas atmosphere. The mixture was stirred at 96 ℃ overnight. After cooling, the mixture was diluted with dichloromethane and washed with water. The organic phase was dried over magnesium sulfate, filtered and the solvent was distilled off under reduced pressure. The crude product was purified by column chromatography using a water/acetonitrile gradient as eluent.
1 H-NMR(400MHz,D6-DMSO)δppm:1.30(t,3H),3.78(q,2H),4.00(s,3H),4.32(s,3H),7.74(d,1H),8.09-8.13(m,1H),8.18(d,1H),8.26(s,1H),9.23(s,1H)。
2- [5- (ethylsulfonyl) -2- (6-fluoropyridin-3-yl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-019)
Figure GDA0003969167050001162
200mg (0.44 mmol) of 2- [ 2-bromo-5- (ethylsulfonyl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-004), 62mg (0.44 mmol) (6-fluoropyridin-3-yl) boronic acid and 15mg (0.01 mmol) of tetrakis (triphenylphosphine) palladium are initially added to a mixture of degassed dioxane (4 ml) and degassed aqueous sodium carbonate (1M, 1.8ml) under a protective gas atmosphere. The mixture was stirred at 96 ℃ overnight. After cooling, the mixture was diluted with dichloromethane and washed with water. The organic phase was dried over magnesium sulfate, filtered and the solvent was distilled off under reduced pressure. The crude product was purified by column chromatography using a cyclohexane/acetone gradient as eluent.
1 H-NMR(400MHz,D6-DMSO)δppm:1.33(t,3H),3.82(q,2H),3.98(s,3H),4.02(s,3H),7.45-7.48(m,1H),8.26(s,1H),8.44-8.48(m,1H),8.71-8.72(m,1H),9.23(s,1H)。
2- [5- (ethylsulfonyl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-029) and 2- [2- (4-chloro-1H-pyrazol-1-yl) -5- (ethylsulfonyl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-027)
Figure GDA0003969167050001171
200mg (0.44 mmol) 2- [ 2-bromo-5- (ethylsulfonyl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-004), 45mg (0.44 mmol) 4-chloro-1H-pyrazole, 4mg (0.02 mmol) copper (I) iodide, 128mg (0.92 mmol) potassium carbonate and 13mg (0.08 mmol) trans-N, N' -dimethylcyclohexane-1, 2-diamine (racemic) are initially charged to degassed dioxane (2 ml) under a protective gas atmosphere. The mixture was stirred at 96 ℃ overnight. After cooling, the mixture was diluted with dichloromethane and washed with water. The organic phase was dried over magnesium sulfate, filtered and the solvent was distilled off under reduced pressure. The crude product was purified by column chromatography using a water/acetonitrile gradient as eluent.
I-029: 1 H-NMR(400MHz,D6-DMSO)δppm:1.27(t,3H),3.80(q,2H),3.97(s,3H),3.99(s,3H),8.23(s,1H),8.32(s,1H),9.21(s,1H)。
I-027: 1 H-NMR(400MHz,D6-DMSO)δppm:1.32(t,3H),3.83(q,2H),3.99(s,3H),4.01(s,3H),8.17(s,1H),8.27(s,1H),8.72(s,1H),9.24(s,1H)。
5- (ethylsulfanyl) -1-methyl-4- [ 3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridin-2-yl ] -1H-imidazole-2-carboxylic acid methyl ester (I-035)
Figure GDA0003969167050001181
4.58g (10.8 mmol) of 2- [ 2-bromo-5- (ethylsulfanyl) -1-methyl-1H-imidazol-4-yl ] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridine (I-010) in methanol (458 ml) are initially charged in a 600ml autoclave. Then 1.67g (20.3 mmol) of sodium acetate and 861mg (1.09 mmol) of [ (diphenylphosphino) ferrocene ] dichloropalladium (II) -acetone adduct are added. The reaction mixture was carbonylated under an atmosphere of carbon monoxide at 5bar and 50 ℃ for 24 hours. After cooling to room temperature, pressure equilibration and removal of the carbon monoxide atmosphere, the mixture was filtered through celite and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using a cyclohexane/acetone gradient as eluent.
1 H-NMR(400MHz,D6-DMSO)δppm:1.10(t,3H),3.04(q,2H),3.92(s,3H),4.08(s,3H),4.18(s,3H),8.22(s,1H),9.17(s,1H)。
5- (ethylsulfonyl) -1-methyl-4- [ 3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridin-2-yl ] -1H-imidazole-2-carboxylic acid methyl ester (I-036)
Figure GDA0003969167050001182
To a solution of 1.60g (3.44 mmol) of methyl 5- (ethylsulfanyl) -1-methyl-4- [ 3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridin-2-yl ] -1H-imidazole-2-carboxylate (I-035) in dichloromethane (80 ml) are added 0.7ml (17.2 mmol) of formic acid and 2.1ml (24.1 mmol, 35% strength in water) of hydrogen peroxide. The mixture was stirred at room temperature overnight and the reaction was quenched by the addition of saturated sodium thiosulfate solution. The organic phase was separated, dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using a cyclohexane/acetone gradient as eluent.
1 H-NMR(400MHz,D6-DMSO)δppm:1.27(t,3H),3.76(q,2H),3.93(s,3H),3.94(s,3H),4.24(s,3H),8.26(s,1H),9.23(s,1H)。
5- (ethylsulfonyl) -1-methyl-4- [ 3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridin-2-yl ] -1H-imidazole-2-carboxamide (I-038)
Figure GDA0003969167050001191
To a solution of 300mg (0.69 mmol) methyl 5- (ethylsulfonyl) -1-methyl-4- [ 3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridin-2-yl ] -1H-imidazole-2-carboxylate (I-036) in methanol (15 ml) and tetrahydrofuran (15 ml) was added 474mg (6.95mmol, 25%) aqueous ammonia. The mixture was stirred at room temperature overnight, and the product was obtained by concentrating the mixture to dryness under reduced pressure.
1 H-NMR(400MHz,D6-DMSO)δppm:1.27(t,3H),3.75(q,2H),3.98(s,3H),4.28(s,3H),8.02(s,1H),8.25(s,1H),8.33(s,1H),9.24(s,1H)。
5- (ethylsulfonyl) -1-methyl-4- [ 3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridin-2-yl ] -1H-imidazole-2-carbonitrile (I-045)
Figure GDA0003969167050001192
A solution of 100mg (0.24 mmol) 5- (ethylsulfonyl) -1-methyl-4- [ 3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridin-2-yl ] -1H-imidazole-2-carboxamide (I-038) in phosphorus oxychloride (2 ml) is stirred at room temperature for 3 days and then concentrated to dryness. The crude product was purified by column chromatography using water/acetonitrile as eluent.
1 H-NMR(400MHz,D6-DMSO)δppm:1.30(t,3H),3.86(q,2H),4.00(s,3H),4.09(s,3H),8.28(s,1H),9.25(s,1H)。
5- (ethylsulfonyl) -1-methyl-4- [ 3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridin-2-yl ] -1H-imidazole-2-carbothioamide (I-046)
Figure GDA0003969167050001193
107mg (0.26 mmol) of 2, 4-bis (4-methoxyphenyl) -1,3,2, 4-dithiodiphosphetane 2, 4-disulfide (Lawson's reagent) are added under a protective gas atmosphere to a solution of 100mg (0.24 mmol) of 5- (ethylsulfonyl) -1-methyl-4- [ 3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c ] pyridin-2-yl ] -1H-imidazole-2-carboxamide (I-038) in toluene (1 ml). The mixture was heated to boiling for 4h, cooled to room temperature, and concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with water. The organic phase was separated, dried over magnesium sulfate, filtered and the solvent was distilled off under reduced pressure. The crude product was purified by column chromatography using a water/acetonitrile gradient as eluent.
1 H-NMR(400MHz,D6-DMSO)δppm:1.29(t,3H),3.81(q,2H),3.99(s,3H),4.14(s,3H),8.25(s,1H),9.23(s,1H),10.10(s,1H),10.60(s,1H)。
In analogy to the examples and according to the preparation described above, the following compounds of formula (I) are obtained:
Figure GDA0003969167050001201
Figure GDA0003969167050001211
Figure GDA0003969167050001221
Figure GDA0003969167050001231
Figure GDA0003969167050001241
Figure GDA0003969167050001251
Figure GDA0003969167050001261
Figure GDA0003969167050001271
Figure GDA0003969167050001281
Figure GDA0003969167050001291
Figure GDA0003969167050001301
Figure GDA0003969167050001311
Figure GDA0003969167050001321
Figure GDA0003969167050001331
Figure GDA0003969167050001341
Figure GDA0003969167050001351
Figure GDA0003969167050001361
NMR data for selected examples
NMR peak list method
The 1H NMR data for selected examples are recorded in the form of a list of 1H NMR peaks. For each signal peak, the δ values in ppm are listed first, followed by the signal intensities in parentheses. The delta value-signal intensity number pairs for different signal peaks are listed as a semicolon separation from each other.
Thus, the peak list of one embodiment takes the form:
δ 1 (strength) 1 )；δ 2 (intensity) 2 )；……；δ i (intensity) i )；……；δ n (strength) n )
In a printed embodiment of the NMR spectrum in cm, the intensity of the sharp signal is highly correlated with the signal, which indicates the true proportion of the signal intensity. In the case of a broad signal, multiple peaks or the middle of the signal and its relative intensity can be shown compared to the strongest signal in the spectrum.
To calibrate the chemical shifts of the 1H NMR spectra, we used the chemical shifts of tetramethylsilane and/or solvent, especially in the case of spectra measured in DMSO. Thus, tetramethylsilane peaks may, but need not, appear in the NMR peak list.
The list of 1H NMR peaks is similar to conventional 1H NMR printed images and therefore, typically contains all the peaks listed in the conventional NMR specification.
In addition, it may show solvent signals, signals of stereoisomers of the target compound (which likewise form part of the subject matter of the present invention), and/or impurity peaks, as in the printed image of conventional 1H NMR.
In the report of compound signals in the delta range of solvent and/or water, our list of 1H NMR peaks shows general solvent peaks, e.g. in DMSO-D 6 DMSO peak in (b) and water peak, which generally have high average intensity.
The peaks of stereoisomers of the target compound and/or impurity peaks typically have a lower average intensity than the peaks of the target compound (e.g. with a purity of > 90%).
These stereoisomers and/or impurities may be unique to a particular manufacturing process. Thus, their peaks can be compared to a "by-product fingerprint" to help identify the reproducibility of our preparation method.
If desired, an expert who calculates the peak of the target compound by known methods (MestreC, ACD simulation, and empirically estimated expected values) can optionally isolate the peak of the target compound using additional intensity filters. This separation is similar to the pick-up of the correlation peak in conventional 1H NMR specifications.
Additional details of the 1H NMR peak list can be found in Research Disclosure Database Number 564025.
Examples of the use
Ctenocephalides felis (Ctenocephalides felis) -in vitro contact test with adult fleas
To coat the test tubes, 9mg of active ingredient are first dissolved in 1ml of analytically pure acetone and then diluted to the desired concentration with analytically pure acetone. Mu.l of the solution was distributed evenly on the inner wall and bottom of a 25ml glass tube by rotation and shaking on an orbital shaker (shaking at a shaking rotation speed of 30rpm for 2 h). 900ppm of active ingredient solution and 44.7cm were used 2 Inner surface, if distributed allHomogenizing, then obtaining 5 mug/cm based on area 2 The dosage of (a).
After the solvent has evaporated, 5-10 adult cat fleas (Ctenocephalides felis) are placed in the tube, sealed with a perforated plastic cap, and incubated horizontally at room temperature and ambient humidity. After 48h, efficacy was determined. To do this, the test tube is placed vertically and fleas are knocked to the bottom of the test tube. Fleas that remained static or moved in an inconsistent manner at the bottom of the tube were considered dead or about to die.
If in this test at 5. Mu.g/cm 2 At an application rate of at least 80% efficacy is obtained, the substance has good efficacy against Ctenocephalides felis. 100% efficacy means that all fleas die or are about to die. Efficacy of 0% means that no fleas are harmed.
In this test, for example, the following compounds from the preparation examples were at 5. Mu.g/cm 2 (500 g/ha) showed 100% efficacy at an application rate of (= 500 g/ha): i-003, I-005, I-007, I-009, I-011, I-013, I-014, I-015, I-018, I-019, I-020, I-022, I-023
Boophilus microplus injection test
Solvent: dimethyl sulfoxide
To prepare a suitable active ingredient preparation, 10mg of active ingredient are mixed with 0.5ml of solvent and the concentrate is diluted with solvent to the desired concentration.
Mu.l of the active ingredient solution were injected into the abdominal cavity of 5 saturated adult female cattle ticks (Boophilus microplus). The animals were transferred to trays and placed in a climate controlled room.
Efficacy was assessed 7 days later by oviposition of fertilized eggs. Eggs that are not significantly fertile are stored in a climate controlled box until the larvae hatch out after about 42 days. 100% efficacy means that no ticks produce any fertilized eggs, 0% means that all eggs are fertile.
In this test, for example, the following compounds from the preparation examples show 100% efficacy at an application rate of 20 μ g/animal: i-041
In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 20 μ g/animal: i-016
Ctenocephalides felis-oral test
Solvent: dimethyl sulfoxide
To prepare a suitable active ingredient preparation, 10mg of active ingredient are mixed with 0.5ml of dimethyl sulfoxide. Diluting with citrated bovine blood to obtain the desired concentration.
Approximately 20 adult unphaged cat fleas (Ctenocephalides felis) were placed in a container sealed with gauze at the top and bottom. A metal cylinder sealed at the bottom with parafilm was placed on the container. The cylinder contains a blood/active ingredient formulation that can be absorbed by fleas through the paraffin film.
After 2 days, the kill rate in% was determined. 100% means that all fleas have been killed, 0% means that none of the fleas have been killed.
In this test, for example, the following compounds from the preparation examples show 100% efficacy at an application rate of 100 ppm: i-003, I-005, I-011, I-013, I-014, I-015, I-018, I-020, I-023, I-033, I-038, I-039 and I-055
In this test, for example, the following compounds from the preparation examples show an efficacy of 95% at an application rate of 100 ppm: i-007, I-009, I-019, I-022, I-029
In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 100 ppm: i-040
In this test, for example, the following compounds from the preparation examples show an efficacy of 80% at an application rate of 100 ppm: i-025, I-049
Lucilia cuprina (Lucilia cuprina) test
Solvent: dimethyl sulfoxide
To prepare a suitable active ingredient preparation, 10mg of active ingredient are mixed with 0.5ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
L1 larvae of approximately 20 Australian blowflies (Australian sheep blowfly) were transferred to test containers containing minced horse meat and the active ingredient formulation at the required concentration.
After 2 days, the kill rate in% was determined. 100% means that all larvae have been killed, 0% means that no larvae have been killed.
In this test, for example, the following compounds from the preparation examples show 100% efficacy at an application rate of 100 ppm: i-001, I-003, I-005, I-007, I-008, I-009, I-011, I-012, I-013, I-014, I-015, I-016, I-018, I-019, I-020, I-022, I-023, I-030, I-033, I-040, I-043, I-049, I-055, I-092
In this test, for example, the following compounds from the preparation examples show an efficacy of 95% at an application rate of 100 ppm: i-029, I-046
In this test, for example, the following compounds from the preparation examples show an efficacy of 80% at an application rate of 100 ppm: i-021
Musca domestica (Musca domestica) test
Solvent: dimethyl sulfoxide
To prepare a suitable active ingredient preparation, 10mg of active ingredient are mixed with 0.5ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
10 adult houseflies (houseflies) were placed in a container containing the sponge treated with the sugar solution and the active ingredient preparation at the desired concentration.
After 2 days, the kill rate in% was determined. 100% means that all flies have been killed, 0% means that none of the flies have been killed.
In this test, for example, the following compounds from the preparation examples show 100% efficacy at an application rate of 100 ppm: i-005 and I-019
In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 100 ppm: i-033
In this test, for example, the following compounds from the preparation examples show an efficacy of 80% at an application rate of 100 ppm: i-009, I-014, I-018, I-049
Myzus persicae (Myzus persicae) -oral test
Solvent: 100 parts by weight of acetone
To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and made up to the desired concentration with water.
50. Mu.l of the active compound preparation are transferred to microtiter plates and supplemented with 150. Mu.l of IPL41 insect medium (33% +15% sugar) to a final volume of 200. Mu.l. Subsequently, the plate was sealed with parafilm and a mixed population of green peach aphids (Myzus persicae) in a second microtiter plate could pierce the parafilm and draw the solution through the parafilm.
After 5 days, the efficacy in% was determined. 100% means that all myzus persicae have been killed; 0% means that no myzus persicae was killed.
In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 4 ppm: i-001, I-002, I-003, I-004, I-005, I-007, I-008, I-009, I-011, I-012, I-013, I-014, I-015, I-016, I-017, I-018, I-019, I-020, I-021, I-022, I-023, I-025, I-026, I-027, I-028, I-029, I-030, I-031, I-032, I-033, I-034, I-036, I-038, I-039, I-040, I-041, I-042, I-043, I-044, I-045I-046, I-047, I-048, I-049, I-051, I-052, I-053, I-055, I-056, I-057, I-058, I-059, I-060, I-061, I-062, I-063, I-064, I-065, I-066, I-067, I-068, I-069, I-070, I-072, I-075, I-079, I-080, I-081, I-082, I-084, I-085, I-086, I-087, I-092, I-093, I-094, I-095, I-097, I-098
In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 4 ppm: i-024, I-037, I-050, I-054, I-078 and I-096
Myzus persicae-spray test
Solvent: 78 parts by weight of acetone
1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether
To prepare a suitable active ingredient preparation, 1 part by weight of active ingredient is dissolved using the abovementioned parts by weight of solvent and made up to the desired concentration with water containing emulsifier at a concentration of 1000 ppm. To prepare other concentrations tested, the formulations were diluted with water containing an emulsifier.
The active ingredient preparation of a desired concentration was sprayed on the leaf surfaces of chinese cabbage (cabbage) leaves infected with all stages of green peach aphid (Myzus persicae).
After 5 days, the efficacy in% was determined. 100% means that all myzus persicae have been killed, 0% means that none of the myzus persicae have been killed.
In this test, for example, the following compounds from the preparation examples show 100% efficacy at an application rate of 100 g/ha: i-011, I-014, I-016, I-017, I-018, I-019, I-020, I-021, I-022, I-023, I-030, I-036, I-039, I-040, I-047, I-059, I-060, I-061, I-062, I-063, I-064, I-065, I-067, I-070, I-076
In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 100 g/ha: i-003, I-005, I-007, I-008, I-009, I-012, I-013, I-015, I-026, I-027, I-028, I-033, I-034, I-038, I-041, I-042, I-043, I-048, I-049, I-050, I-051, I-055, I-057, I-058, I-069, I-071, I-074, I-075, I-077, I-079, I-082, I-084, I-085, I-086, I-095, I-096 in this test, for example, the following compounds from the preparation examples show an efficacy of 70% at an application rate of 100 g/ha: i-029, I-066
Horseradish Simon Jack (Phaedon cochlearia) — spray test
Solvent: 78 parts by weight of acetone
1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether
To prepare a suitable active ingredient preparation, 1 part by weight of active ingredient is dissolved using the abovementioned parts by weight of solvent, the desired concentration being made up with water containing emulsifier at a concentration of 1000 ppm. To prepare other concentrations tested, the formulations were diluted with water containing an emulsifier.
Spraying active ingredient preparation with desired concentration on leaf surface of folium Brassicae Pekinensis (Chinese cabbage), drying, and adding larva of mustard beetle (Armoracia rusticana).
After 7 days, the efficacy in% was determined. 100% means that all beetle larvae have been killed, 0% means that none of the beetle larvae have been killed.
In this test, for example, the following compounds from the preparation examples show an efficacy of 83% at an application rate of 500 g/h: i-066
In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 g/h: i-005, I-007, I-011, I-013, I-014, I-015, I-018, I-019, I-020, I-022, I-023, I-024, I-026, I-027, I-028, I-029, I-036, I-038, I-041, I-042, I-046, I-049, I-055, I-057, I-059, I-060, I-061, I-062, I-063, I-067, I-068, I-069, I-070, I-076, I-077, I-078, I-080, I-081, I-082, I-087, I-093, I-096, I-098
In this test, for example, the following compounds from the preparation examples show an efficacy of 83% at an application rate of 100 g/h: i-035, I-064, I-079, I-094
In this test, for example, the following compounds from the preparation examples show an efficacy of 67% at an application rate of 100 g/h: i-092.
Spodoptera frugiperda (Spodoptera frugiperda) — spray test
Solvent: 78 parts by weight of acetone
1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether
To prepare a suitable active ingredient preparation, 1 part by weight of active ingredient is dissolved using the abovementioned parts by weight of solvent and made up to the desired concentration with water containing emulsifier at a concentration of 1000 ppm. To prepare other concentrations tested, the formulations were diluted with water containing an emulsifier.
The preparation of active ingredient with desired concentration is sprayed on leaves of corn (Zea mays), dried, and put into caterpillars of Spodoptera frugiperda (Spodoptera frugiperda).
After 7 days, the efficacy in% was determined. 100% means that all caterpillars have been killed, 0% means that none of the caterpillars have been killed.
In this test, for example, the following compounds from the preparation examples show 100% efficacy at an application rate of 100 g/ha: i-005, I-007, I-011, I-014, I-015, I-019, I-024, I-025, I-027, I-033, I-063, I-069, I-076, I-078, I-081, I-087, I-092, I-093, I-094, I-095, I-097, I-098
In this test, for example, the following compounds from the preparation examples show an efficacy of 83% at an application rate of 100 g/ha: i-018, I-020, I-060, I-070, I-082 and I-096
In this test, for example, the following compounds from the preparation examples show an efficacy of 67% at an application rate of 100 g/ha: i-057
Tetranychus urticae (Tetranychus urticae) — spray test, OP-resistance
Solvent: 78.0 parts by weight of acetone
1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether
To prepare a suitable active ingredient preparation, 1 part by weight of active ingredient is dissolved using the abovementioned parts by weight of solvent, the desired concentration being made up with water containing emulsifier at a concentration of 1000 ppm. To prepare other concentrations tested, the formulations were diluted with water containing an emulsifier.
The preparation of active ingredient of the desired concentration is sprayed on the leaf surface of the leaves of kidney beans (Phaseolus vulgaris) infested with all stages of spider mites red spider mite (tetranychus urticae).
After 6 days, the efficacy in% was determined. 100% means that all spider mites have been killed; 0% means that no spider mites were killed.
In this test, for example, the following compounds from the preparation examples show 100% efficacy at an application rate of 100 g/ha: i-054, I-070, I-077, I-082 and I-092
In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 100 g/ha: i-049, I-050, I-055, I-066, I-074, I-075, I-076, I-086
In this test, for example, the following compounds from the preparation examples show 100% efficacy at an application rate of 20 g/ha: i-082
In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 20 g/ha: i-042, I-049, I-077 and I-087.

Claims (9)

1. A compound of formula (I)
Figure FDA0003969167040000011
Wherein:
R 1 is (C) 1 -C 6 ) An alkyl group, a carboxyl group,
R 2 is hydrogen or (C) 1 -C 6 ) An alkyl group, which is a radical of an alkyl group,
R 3 is hydrogen, halogen, cyano, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxycarbonyl, aminocarbonyl, (C) 1 -C 6 ) Alkylaminocarbonyl, di (C) 1 -C 6 ) Alkylaminocarbonyl, (C) 1 -C 6 ) Haloalkylaminocarbonyl, aminothiocarbonyl, (C) 1 -C 6 ) Alkylamino thiocarbonyl, di (C) 1 -C 6 ) Alkylaminothiocarbonyl group, (C) 2 -C 6 ) Alkenyl, (C) 3 -C 8 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkynyl or (C) 3 -C 6 ) Cycloalkyl- (C) 1 -C 6 ) An alkyl group, which is a radical of an alkyl group,
or is phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, pyrazolyl, thiazolyl, imidazolyl, pyrrolyl or cyclohexenyl, each of which is optionally mono-or polysubstituted by identical or different substituents, wherein the substituents are in each case as follows: cyano, halogen, (C) 3 -C 8 ) Cycloalkyl, cyano (C) 3 -C 8 ) Cycloalkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) A cyanoalkyl group or an aminocarbonyl group,
X is a heteroaromatic 9-membered fused bicyclic ring system selected from Q1, Q7, Q8, Q9 or Q12
Figure FDA0003969167040000012
R 4 Is hydrogen or (C) 1 -C 6 ) An alkyl group, which is a radical of an alkyl group,
R 5 、R 6 independently is hydrogen or (C) 1 -C 6 ) A halogenated alkyl group,
n is 0 or 2.
2. A compound of formula (I) according to claim 1, wherein
R 1 Is (C) 1 -C 4 ) An alkyl group, a carboxyl group,
R 2 is hydrogen or (C) 1 -C 4 ) An alkyl group, a carboxyl group,
R 3 is hydrogen, halogen, cyano, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkoxycarbonyl, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Haloalkylaminocarbonyl, aminothiocarbonyl, (C) 1 -C 4 ) Alkylamino thiocarbonyl, di (C) 1 -C 4 ) Alkylaminothiocarbonyl group, (C) 2 -C 4 ) Alkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkynyl or (C) 3 -C 6 ) Cycloalkyl- (C) 1 -C 4 ) An alkyl group, which is a radical of an alkyl group,
or is phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, pyrazolyl, thiazolyl, imidazolyl, pyrrolyl or cyclohexenyl, each of which is optionally mono-or polysubstituted by identical or different substituents, where in each case the substituents are as follows: cyano, halogen, (C) 3 -C 6 ) Cycloalkyl, cyano (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) A cyanoalkyl group or an aminocarbonyl group,
x is a heteroaryl 9-membered fused bicyclic ring system selected from Q1, Q7, Q8, Q9 or Q12,
R 4 Is hydrogen or (C) 1 -C 4 ) An alkyl group, which is a radical of an alkyl group,
R 5 、R 6 each independently is hydrogen or (C) 1 -C 4 ) A halogenated alkyl group,
n is 0 or 2.
3. A compound of formula (I) according to claim 1, wherein
R 1 Is (C) 1 -C 4 ) An alkyl group, a carboxyl group,
R 2 is hydrogen or (C) 1 -C 4 ) An alkyl group, a carboxyl group,
R 3 is hydrogen, halogen, cyano, (C) 1 -C 4 ) Alkyl, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Haloalkylaminocarbonyl group, (C) 2 -C 4 ) Alkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkynyl, (C) 3 -C 6 ) Cycloalkyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkoxycarbonyl, aminothiocarbonyl, (C) 1 -C 4 ) Alkylamino thiocarbonyl or di (C) 1 -C 4 ) An alkylamino-thiocarbonyl group, an amino group,
or isPhenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, pyrazolyl, thiazolyl, imidazolyl, pyrrolyl or cyclohexenyl, each of which is optionally mono-or polysubstituted by identical or different substituents, wherein in each case the substituents are as follows: cyano, halogen, (C) 3 -C 6 ) Cycloalkyl, cyano (C) 3 -C 6 ) Cycloalkyl group, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) A cyanoalkyl group or an aminocarbonyl group,
x is a heteroaromatic 9-membered fused bicyclic ring system selected from Q1, Q7, Q8, Q9 or Q12,
R 4 is hydrogen or (C) 1 -C 4 ) An alkyl group, a carboxyl group,
R 5 is (C) 1 -C 4 ) A halogenated alkyl group,
R 6 is a hydrogen, and is,
n is 0 or 2.
4. A compound of formula (I) according to claim 1, wherein
R 1 Is methyl, ethyl, n-propyl or isopropyl,
R 2 hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl,
R 3 is hydrogen, (C) 1 -C 4 ) Alkyl, (C) 2 -C 4 ) Alkenyl, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkenyl, halogen, cyano, (C) 3 -C 6 ) Cycloalkyl- (C) 2 ) Alkynyl, (C) 3 -C 6 ) Cycloalkyl- (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Alkoxycarbonyl, aminocarbonyl, (C) 1 -C 4 ) Alkylaminocarbonyl, di (C) 1 -C 4 ) Alkylaminocarbonyl, (C) 1 -C 4 ) Haloalkylaminocarbonyl, aminothiocarbonyl, (C) 1 -C 4 ) Alkylaminothiocarbonyl or di (C) 1 -C 4 ) An alkylamino-thiocarbonyl group, an amino group,
or is phenyl, pyridyl, pyrimidinyl, pyridazinyl,Thienyl, thiazolyl, imidazolyl, pyrazolyl, pyrrolyl or cyclohexenyl, each of which is optionally mono-or polysubstituted by identical or different substituents and bridged to the remainder of the molecule via a carbon atom, wherein the substituents in each case are as follows: cyano, halogen, (C) 3 -C 6 ) Cycloalkyl, cyano (C) 3 -C 6 ) Cycloalkyl, (C) 1 -C 4 ) Alkyl, (C) 1 -C 4 ) Haloalkyl, (C) 1 -C 4 ) A cyanoalkyl group or an aminocarbonyl group,
or pyrazolyl or imidazolyl, each of which is optionally mono-or polysubstituted by identical or different substituents and bridged to the remainder of the molecule via a nitrogen atom, wherein the substituents in each case are as follows: the halogen(s) are selected from the group consisting of,
X is Q1, Q7, Q8, Q9 or Q12,
R 4 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl,
R 5 is fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R 6 is a hydrogen atom, and is,
n is 0 or 2.
5. A compound of formula (I) according to claim 1, wherein
R 1 Is an ethyl group or an isopropyl group,
R 2 is a methyl group, an ethyl group or an isopropyl group,
R 3 hydrogen, bromine, cyano, ethenyl, cyclopropylethenyl, isopropenyl, cyclopropylethynyl, methyl, ethyl, isopropyl, cyclopropylethyl, methoxycarbonyl, trifluoroethylaminocarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, aminothiocarbonyl, methylaminothiocarbonyl, dimethylaminothiocarbonyl,
or is phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl (thienyl), thiazolyl, imidazolyl, pyrazolyl, pyrrolyl or cyclohexenyl, each of which is optionally mono-, di-or tri-substituted by identical or different substituents and is bridged to the remainder of the molecule via a carbon atom, wherein the substituents in each case are as follows: cyano, fluorine, chlorine, methyl, cyclopropyl, cyanomethyl, cyanoisopropyl, cyanocyclopropyl, trifluoromethyl, trifluoroethyl, aminocarbonyl or is pyrazolyl or imidazolyl, each of which is optionally monosubstituted by chlorine and is bridged to the remainder of the molecule via a nitrogen atom,
X is Q1, Q7, Q8, Q9 or Q12,
R 4 is a methyl group, and the compound is,
R 5 is a trifluoromethyl group, and is a trifluoromethyl group,
R 6 is a hydrogen, and is,
n is 0 or 2.
6. The compound of formula (I) according to claim 1, having the structure:
Figure FDA0003969167040000041
Figure FDA0003969167040000051
Figure FDA0003969167040000061
Figure FDA0003969167040000071
Figure FDA0003969167040000081
Figure FDA0003969167040000091
Figure FDA0003969167040000101
Figure FDA0003969167040000111
Figure FDA0003969167040000121
Figure FDA0003969167040000131
Figure FDA0003969167040000141
Figure FDA0003969167040000151
Figure FDA0003969167040000161
Figure FDA0003969167040000171
7. an agrochemical formulation comprising a compound of formula (I) as claimed in claim 1 and an extender and/or a surfactant.
8. A method for controlling animal pests, characterized in that a compound of the formula (I) according to claim 1 or an agrochemical according to claim 7 is allowed to act on the animal pests and/or their habitat.
9. Use of a compound of the formula (I) according to claim 1 or an agrochemical according to claim 7 for controlling animal pests.
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